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Journal articles on the topic 'Ortho-quinone methides'

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Author: Grafiati

Published: 10 December 2022

Last updated: 28 January 2023

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1

Chambers, Jeffrey D., Jason Crawford, Haydn W. R. Williams, Claude Dufresne, John Scheigetz, Michael A. Bernstein, and Cheuk K. Lau. "Reactions of 2-phenyl-4H-1,3,2-benzodioxaborin, a stable ortho-quinone methide precursor." Canadian Journal of Chemistry 70, no. 6 (June 1, 1992): 1717–32. http://dx.doi.org/10.1139/v92-216.

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Thermolysis of 1-phenyl-4H-1,3,2-benzodioxaborins generated the corresponding ortho-quinone methides, which were found to undergo intermolecular cycloaddition reactions with ethyl vinyl ether, dihydropyran, β-methylstyrene, cyclohexene, and 1-ethoxy-1-z-trimethylsiloxy-1-propenes to give various substituted chromans. Intramolecular trapping of the quinone methides with an olefin led to the syntheses of several analogs of tetrahydrocannabinols. ortho-Quinone methides, generated by treatment of the 2-phenyl-4H-1,3,2-benzodioxaborins with a Lewis acid, react with various nucleophiles to give the corresponding 1,4-addition products. Thus, alkyl and aryl thiols, alcohols, amine, hydride, allyl trimethylsilane, acetophenone, and diethylmalonate as well as some aryl compounds react with the quinone methide to give various 2-substituted phenols. Intramolecular reaction of the quinone methide with an aryl group led to the preparation of some 4-phenylchromans and tetralins.

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2

Wan, Peter, Beverly Barker, Li Diao, Maike Fischer, Yijian Shi, and Cheng Yang. "1995 Merck Frosst Award Lecture Quinone methides: relevant intermediates in organic chemistry." Canadian Journal of Chemistry 74, no. 4 (April 1, 1996): 465–75. http://dx.doi.org/10.1139/v96-051.

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ortho and para-Quinone methides (2-methylene-3,5-cyclohexadien-1-one and 4-methylene-2,5-cyclohexadien-1-one, respectively) are intermediates in a variety of important chemical systems. In particular, o-quinone methides are useful in synthesis for the construction of chroman ring systems. A brief account of the relevance of quinone methide chemistry will be provided. This is followed by a review of recent studies from our laboratory on efficient methods for the photogeneration of quinone methides, concentrating on the use of hydroxy-substituted benzyl alcohols in aqueous media. It is shown that this method is general since it provides access to o-, m-, and p-quinone methide isomers. When appropriately substituted, all of these quinone methide isomers have been spectroscopically characterized by laser flash photolysis, making this technique the one of choice for studying the dynamics of these reactive intermediates. The mechanism of photochemical generation from hydroxybenzyl alcohols and extensions of the reaction to photogeneration of fluorenyl and biphenyl quinone methides will also be presented. Key words: quinone methide, biphenyl quinone methide, carbocation, photosolvolysis, photodehydroxylation, hetero-Diels–Alder reaction.

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3

Spivey, Alan, Christian Nielsen, and Hossay Abas. "Stereoselective Reactions of ortho-Quinone Methide and ortho-Quinone Methide Imines and Their Utility in Natural Product Synthesis." Synthesis 50, no. 20 (August 14, 2018): 4008–18. http://dx.doi.org/10.1055/s-0037-1610241.

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Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and reaction as well as recent applications in total synthesis are discussed.1 Introduction2 Conjugate Addition Reactions3 Concerted Cycloaddition Reactions4 Stepwise Addition Reactions5 Applications in Total Synthesis6 Conclusion

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4

Huang, Hong-Ming, Xu-Yan Wu, Bo-Rong Leng, Yi-Long Zhu, Xin-Chao Meng, Yu Hong, Bo Jiang, and De-Cai Wang. "Cu(ii)-Catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles." Organic Chemistry Frontiers 7, no. 2 (2020): 414–19. http://dx.doi.org/10.1039/c9qo01343a.

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A new Cu(ii)-catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established.

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5

Bai, Wen-Ju, Jonathan G. David, Zhen-Gao Feng, Marisa G. Weaver, Kun-Liang Wu, and Thomas R. R. Pettus. "The Domestication of ortho-Quinone Methides." Accounts of Chemical Research 47, no. 12 (December 3, 2014): 3655–64. http://dx.doi.org/10.1021/ar500330x.

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6

Tanaka, Kenta, Yosuke Asada, and Yujiro Hoshino. "A new cycloaddition profile for ortho-quinone methides: photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo[b]cyclopenta[e]oxepines." Chemical Communications 58, no. 15 (2022): 2476–79. http://dx.doi.org/10.1039/d1cc06332d.

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7

Liang, Dong, Li-Ping Tan, Wen-Jing Xiao, and Jia-Rong Chen. "Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines." Chemical Communications 56, no. 26 (2020): 3777–80. http://dx.doi.org/10.1039/d0cc00747a.

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8

Mayer, Martin, Maik Pahl, Matthias Spanka, Max Grellmann, Marcel Sickert, Christoph Schneider, Knut R. Asmis, and Detlev Belder. "Unravelling the configuration of transient ortho-quinone methides by combining microfluidics with gas phase vibrational spectroscopy." Physical Chemistry Chemical Physics 22, no. 8 (2020): 4610–16. http://dx.doi.org/10.1039/c9cp06435d.

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9

Xu, Jianfeng, Shiru Yuan, Jingyi Peng, Maozhong Miao, Zhengkai Chen, and Hongjun Ren. "Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7513–17. http://dx.doi.org/10.1039/c7ob01783a.

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10

Saha, Satyajit, Santosh Kumar Alamsetti, and Christoph Schneider. "Chiral Brønsted acid-catalyzed Friedel–Crafts alkylation of electron-rich arenes with in situ-generated ortho-quinone methides: highly enantioselective synthesis of diarylindolylmethanes and triarylmethanes." Chemical Communications 51, no. 8 (2015): 1461–64. http://dx.doi.org/10.1039/c4cc08559k.

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11

Chen, Renjie, Yu Liu, and Sunliang Cui. "1,4-Conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction." Chemical Communications 54, no. 83 (2018): 11753–56. http://dx.doi.org/10.1039/c8cc07328g.

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12

Gu, Xiu, Hao Yuan, Jun Jiang, Yi Wu, and Wen-Ju Bai. "Catalytic Asymmetric Hydrophosphination of ortho-Quinone Methides." Organic Letters 20, no. 22 (November 6, 2018): 7229–33. http://dx.doi.org/10.1021/acs.orglett.8b03158.

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13

Allen, Emily E., Calvin Zhu, James S. Panek, and Scott E. Schaus. "Multicomponent Condensation Reactions via ortho-Quinone Methides." Organic Letters 19, no. 7 (March 30, 2017): 1878–81. http://dx.doi.org/10.1021/acs.orglett.7b00647.

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14

Willis, Nicky J., and Christopher D. Bray. "ortho-Quinone Methides in Natural Product Synthesis." Chemistry - A European Journal 18, no. 30 (June 15, 2012): 9160–73. http://dx.doi.org/10.1002/chem.201200619.

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15

Singh, Maya Shankar, Anugula Nagaraju, Namrata Anand, and Sushobhan Chowdhury. "ortho-Quinone methide (o-QM): a highly reactive, ephemeral and versatile intermediate in organic synthesis." RSC Adv. 4, no. 99 (2014): 55924–59. http://dx.doi.org/10.1039/c4ra11444b.

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16

Lian, Xiao-Lei, Alafate Adili, Bin Liu, Zhong-Lin Tao, and Zhi-Yong Han. "Enantioselective [4 + 1] cycloaddition of ortho-quinone methides and bromomalonates under phase-transfer catalysis." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3670–73. http://dx.doi.org/10.1039/c7ob00484b.

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17

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (May 14, 2020): 2311–29. http://dx.doi.org/10.1055/s-0040-1707115.

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Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and aryloxepines are also discussed.1 Introduction2 Benzyl Reagents with Leaving Groups3 Quinone Methide Mediated Reactions4 Arylation of Benzyl Halides5 C–H Activation of Methylene6 Reactions of Carbonyl Compounds7 Conclusions

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18

Cheng, Yuyu, Zhiqiang Fang, Yanwen Jia, Zhongyue Lu, Wenjun Li, and Pengfei Li. "Organocatalytic enantioselective conjugate addition of 2-naphthols to ortho-hydroxyphenyl substituted para-quinone methides: access to unsymmetrical triarylmethanes." RSC Advances 9, no. 42 (2019): 24212–17. http://dx.doi.org/10.1039/c9ra04768a.

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19

Liu, Lina, Zhenbo Yuan, Rui Pan, Yuye Zeng, Aijun Lin, Hequan Yao, and Yue Huang. "1,6-Conjugated addition-mediated [4 + 1] annulation: an approach to 2,3-dihydrobenzofurans." Organic Chemistry Frontiers 5, no. 4 (2018): 623–28. http://dx.doi.org/10.1039/c7qo00846e.

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20

Zhou, Fan, Ying Cheng, Xiao-Peng Liu, Jia-Rong Chen, and Wen-Jing Xiao. "A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis." Chemical Communications 55, no. 21 (2019): 3117–20. http://dx.doi.org/10.1039/c9cc00727j.

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21

Xia, Chao, Dong-Chao Wang, Gui-Rong Qu, and Hai-Ming Guo. "Palladium-catalyzed enantioselective [5 + 4] annulation of ortho-quinone methides and vinylethylene carbonates." Organic Chemistry Frontiers 7, no. 12 (2020): 1474–80. http://dx.doi.org/10.1039/d0qo00128g.

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Highly enantioselective [5 + 4] annulations of ortho-quinone methides with vinylethylene carbonates are enabled by asymmetric palladium catalysis for the synthesis of chiral nine-membered benzo-heterocycles.

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22

Gharui, Chandan, Shreya Singh, and Subhas Chandra Pan. "Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7272–76. http://dx.doi.org/10.1039/c7ob01766a.

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The first organocatalytic asymmetric [4 + 2]-cycloaddition reaction between acyclic enecarbamates with in situ generated ortho-quinone methides has been developed using chiral phosphoric acids as catalysts.

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23

Wang, Junwei, Xiang Pan, Quanjin Rong, Lei Zhao, Lin Zhao, Weichen Dai, Kun Zhao, and Lihong Hu. "One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides." RSC Advances 10, no. 55 (2020): 33455–60. http://dx.doi.org/10.1039/d0ra05497f.

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A facile one-pot synthesis has been developed through alkylation/acylation of ortho-tosylaminophenyl-substituted para-quinone methides followed by an intramolecular 1,6-conjugate addition and oxidation sequence.

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24

You, Yong, Ting-Ting Li, Shu-Pei Yuan, Ke-Xin Xie, Zhen-Hua Wang, Jian-Qiang Zhao, Ming-Qiang Zhou, and Wei-Cheng Yuan. "Catalytic asymmetric [4+2] cycloaddition of 1-((2-aryl)vinyl)naphthalen-2-ols with in situ generated ortho-quinone methides for the synthesis of polysubstituted chromanes." Chemical Communications 56, no. 3 (2020): 439–42. http://dx.doi.org/10.1039/c9cc08316b.

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25

Zhang, Song, Xiaojun Yu, Jianke Pan, Chunhui Jiang, Hongsu Zhang, and Tianli Wang. "Asymmetric synthesis of spiro-structural 2,3-dihydrobenzofurans via the bifunctional phosphonium salt-promoted [4 + 1] cyclization of ortho-quinone methides with α-bromoketones." Organic Chemistry Frontiers 6, no. 22 (2019): 3799–803. http://dx.doi.org/10.1039/c9qo01096c.

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A practical and scalable method for highly stereoselective construction of spiro-2,3-dihydrobenzofurans via cyclization of ortho-quinone methides and α-bromoketones by bifunctional phosphonium salt catalysis was developed.

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26

Tan, Qingfa, Han Yu, Yao Luo, Fenzhen Chang, Xiaohua Liu, Yuqiao Zhou, and Xiaoming Feng. "Asymmetric catalytic [4+3] cycloaddition of ortho-quinone methides with oxiranes." Chemical Communications 57, no. 24 (2021): 3018–21. http://dx.doi.org/10.1039/d1cc00262g.

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27

Lei, Lu, Yu-Feng Liang, Cui Liang, Jiang-Ke Qin, Cheng-Xue Pan, Gui-Fa Su, and Dong-Liang Mo. "Copper(i)-catalyzed [4 + 2] cycloaddition of aza-ortho-quinone methides with bicyclic alkenes." Organic & Biomolecular Chemistry 19, no. 15 (2021): 3379–83. http://dx.doi.org/10.1039/d1ob00319d.

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An efficient copper(i)-catalyzed [4 + 2] cycloaddition of aza-ortho-quinone methides (ao-QMs) and bicyclic alkenes to prepare tetrahydroquinoline-fused bicycles bearing multiple stereocenters in good yields is reported.

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28

Feng, Ziwen, Zhenbo Yuan, Xiaobin Zhao, Yue Huang, and Hequan Yao. "A [4 + 1] annulation of ortho-electrophile-substituted para-quinone methides for the synthesis of indanes and isoindolines." Organic Chemistry Frontiers 6, no. 20 (2019): 3535–39. http://dx.doi.org/10.1039/c9qo00977a.

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Indanes and isoindolines were obtained via a 1,6-conjugated addition/1,4-Michael addition of ortho-electrophile-substituted para-quinone methides with nucleophiles in high yields and with good functional group tolerance.

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29

Xu, Guangyang, Shengbiao Tang, Ying Shao, and Jiangtao Sun. "B(C6F5)3-Catalyzed formal (4+1)-annulation of ortho-quinone methides with diazoacetates: access to 2,3-dihydrobenzofurans." Chemical Communications 55, no. 62 (2019): 9096–99. http://dx.doi.org/10.1039/c9cc04863d.

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30

Zhang, Lili, Xiao Zhou, Pengfei Li, Zhantao Liu, Yang Liu, Yong Sun, and Wenjun Li. "Asymmetric synthesis of chromene skeletons via organocatalytic domino reactions of in situ generated ortho-quinone methide with malononitrile and β-functionalized ketone." RSC Advances 7, no. 62 (2017): 39216–20. http://dx.doi.org/10.1039/c7ra08157j.

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Enantioselective organocatalytic domino reactions of in situ generated ortho-quinone methides with malononitrile and β-functionalized ketones have been developed. This strategy could generate various chiral chromenes in high yields and stereoselectivities.

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31

Duan, Kang, Hongjin Shi, Lin-Xuan Wang, Shuai-Shuai Li, Lubin Xu, and Jian Xiao. "Hydride transfer enabled switchable dearomatization of indoles in the carbocyclic ring and the pyrrole ring." Organic Chemistry Frontiers 7, no. 17 (2020): 2511–17. http://dx.doi.org/10.1039/d0qo00658k.

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Hydride transfer enabled the first success of the regioselective dearomatization of indoles in the carbocyclic ring and the pyrrole ring, which was induced by ortho-quinone methides and vinylogous iminium intermediates, respectively.

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32

Yu, Xuan, Wenjie Lan, Jiaqi Li, Hui Bai, Zhaohai Qin, and Bin Fu. "Enantioselective one-pot synthesis of 4H-chromene derivatives catalyzed by a chiral Ni(ii) complex." RSC Advances 10, no. 72 (2020): 44437–41. http://dx.doi.org/10.1039/d0ra08906k.

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33

Mukhopadhyay, Soumendranath, Chandan Gharui, and Subhas Chandra Pan. "Applications of Bifunctional Organocatalysts on ortho ‐Quinone Methides." Asian Journal of Organic Chemistry 8, no. 11 (September 26, 2019): 1970–84. http://dx.doi.org/10.1002/ajoc.201900466.

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34

Bai, Wen-Ju, Jonathan G. David, Zhen-Gao Feng, Marisa G. Weaver, Kun-Liang Wu, and Thomas R. R. Pettus. "ChemInform Abstract: The Domestication of ortho-Quinone Methides." ChemInform 46, no. 15 (March 26, 2015): no. http://dx.doi.org/10.1002/chin.201515346.

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35

Jha, Babli K., Jaggaraju Prudhviraj, Prathama S. Mainkar, Nagender Punna, and Srivari Chandrasekhar. "Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides." RSC Advances 10, no. 63 (2020): 38588–91. http://dx.doi.org/10.1039/d0ra08289a.

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The first [4 + 1] annulation reaction of in situ-generated highly electrophilic CF₃-ortho-quinone methides with sulphur ylides has been put forth under mild reaction conditions to access CF₃-dihydrobenzofurans.

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36

Carceller-Ferrer, Laura, Gonzalo Blay, José R. Pedro, and Carlos Vila. "Squaramide-Catalyzed Enantioselective Michael Addition of Pyrazol-3- ones to ortho-Quinone Methides." Letters in Organic Chemistry 17, no. 11 (November 29, 2020): 837–44. http://dx.doi.org/10.2174/1876402911666190806105543.

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A bifunctional squaramide catalyzed the enantioselective Michael addition of pyrazol-3- ones to ortho-quinone methides, generated in situ from 2-(1-tosylalkyl)phenols is presented. The corresponding chiral pyrazolones are obtained with good to excellent yields (27-98%) and enantiomeric excess (14-99% ee).

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37

Barta, Petra, Ferenc Fülöp, and István Szatmári. "Mannich base-connected syntheses mediated by ortho-quinone methides." Beilstein Journal of Organic Chemistry 14 (March 6, 2018): 560–75. http://dx.doi.org/10.3762/bjoc.14.43.

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This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dienophile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important pharmacological activities of these reactive o-QM intermediates, special attention is paid to the biological activity of these compounds.

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38

Osipov, D. V., V. A. Osyanin, and Yu N. Klimochkin. "ortho-Quinone methides as key intermediates in cascade heterocyclizations." Russian Chemical Reviews 86, no. 7 (July 27, 2017): 625–87. http://dx.doi.org/10.1070/rcr4679.

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39

Willis, Nicky J., and Christopher D. Bray. "ChemInform Abstract: ortho-Quinone Methides in Natural Product Synthesis." ChemInform 43, no. 46 (October 18, 2012): no. http://dx.doi.org/10.1002/chin.201246243.

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40

Adili, Alafate, Zhong-Lin Tao, Dian-Feng Chen, and Zhi-Yong Han. "Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2247–50. http://dx.doi.org/10.1039/c4ob02602k.

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2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities.

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41

Zhang, Lili, Yang Liu, Kun Liu, Zhantao Liu, Ningning He, and Wenjun Li. "Asymmetric synthesis of dihydrocoumarins via the organocatalytic hetero-Diels–Alder reaction of ortho-quinone methides." Org. Biomol. Chem. 15, no. 41 (2017): 8743–47. http://dx.doi.org/10.1039/c7ob02325a.

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42

Lumb, Jean-Philip, Kevin C. Choong, and Dirk Trauner. "ortho-Quinone Methides frompara-Quinones: Total Synthesis of Rubioncolin B." Journal of the American Chemical Society 130, no. 29 (July 2008): 9230–31. http://dx.doi.org/10.1021/ja803498r.

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43

Uyanik, Muhammet, Kohei Nishioka, Ryutaro Kondo, and Kazuaki Ishihara. "Chemoselective oxidative generation of ortho-quinone methides and tandem transformations." Nature Chemistry 12, no. 4 (March 23, 2020): 353–62. http://dx.doi.org/10.1038/s41557-020-0433-4.

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44

Lewis, Robert S., Christopher J. Garza, Ann T. Dang, Te Kie A. Pedro, and William J. Chain. "Michael Additions of Highly Basic Enolates to ortho-Quinone Methides." Organic Letters 17, no. 9 (April 23, 2015): 2278–81. http://dx.doi.org/10.1021/acs.orglett.5b00972.

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45

Ivanov, Konstantin L., Stanislav I. Bezzubov, Mikhail Ya Melnikov, and Ekaterina M. Budynina. "Donor–acceptor cyclopropanes as ortho-quinone methide equivalents in formal (4 + 2)-cycloaddition to alkenes." Organic & Biomolecular Chemistry 16, no. 21 (2018): 3897–909. http://dx.doi.org/10.1039/c8ob00377g.

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A new reactivity of donor–acceptor cyclopropanes as synthetic equivalents of o-quinone methides was revealed for 2-hydroxyarylcyclopropane diesters in their formal (4 + 2)-cycloaddition to alkenes yielding chromanes.

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46

Zhang, Yueteng, Peng Ji, Xiang Meng, Feng Gao, Fanxun Zeng, and Wei Wang. "Facile Synthesis of 2H-Benzo[h]Chromenes via an Arylamine-Catalyzed Mannich Cyclization Cascade Reaction." Molecules 26, no. 12 (June 12, 2021): 3617. http://dx.doi.org/10.3390/molecules26123617.

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A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

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47

Zhou, Ji, Mao-Lin Wang, Xiang Gao, Guo-Fang Jiang, and Yong-Gui Zhou. "Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols." Chemical Communications 53, no. 25 (2017): 3531–34. http://dx.doi.org/10.1039/c7cc01072a.

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A bifunctional squaramide-catalyzed reaction of azlactones within situgeneratedo-quinone methides has been successfully developed, providing dihydrocoumarins with excellent diastereo- and enantioselectivities.

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48

Hoshino, Yujiro, Kiyoshi Honda, Kenta Tanaka, Ko Ueno, Yuta Tanaka, Naoya Ohtsuka, Yosuke Asada, Mami Kishimoto, and Shuto Sunaga. "Dual In Situ Generation of Aliphatic Vinyl Ethers and Electron-Deficient ortho-Quinone Methides for Inverse-Electron-Demand [4+2] Cycloaddition: A Selective One-Pot Synthesis of 3-Alkylchromanes." Synlett 31, no. 12 (May 6, 2020): 1197–200. http://dx.doi.org/10.1055/s-0040-1707522.

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An inverse-electron-demand [4+2] cycloaddition of in situ generated aliphatic vinyl ethers and electron-deficient ortho-quinone methides (o-QMs) has been developed. The reaction of in situ generated aliphatic vinyl ethers with o-QMs afforded the corresponding 3-alkylchromanes with high stereo- and regioselectivities. The method provides a versatile access to functionalized 3-alkylchromanes and it constitutes a useful tool for the synthesis of biologically active chromanes.

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49

Liu, Si-Jia, Man-Su Tu, Kai-Yue Liu, Jia-Yi Chen, Shao-Fei Ni, Yu-Chen Zhang, and Feng Shi. "Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides." Molecules 26, no. 21 (November 8, 2021): 6751. http://dx.doi.org/10.3390/molecules26216751.

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Abstract:

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.

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50

Ren, Hongjun, Manman Sun, Jinyu Song, Lei Wang, Wenguang Yin, and Maozhong Miao. "Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans." Synlett 31, no. 08 (February 26, 2020): 818–22. http://dx.doi.org/10.1055/s-0039-1691739.

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Abstract:

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

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