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Artykuły w czasopismach na temat „Allylic alcohols”

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Autor: Grafiati

Data publikacji: 4 czerwca 2021

Data aktualizacji: 18 lutego 2022

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1

Ficeri, Vlastimír, Peter Kutschy, Milan Dzurilla i Ján Imrich. "[3,3]- Versus [1,3]-Sigmatropic Rearrangement of O-Substituted Allyl N-Acylmonothiocarbamates". Collection of Czechoslovak Chemical Communications 59, nr 12 (1994): 2650–62. http://dx.doi.org/10.1135/cccc19942650.

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Substituted allylic alcohols (2-buten-1-ol, 1-buten-3-ol, cinnamyl alcohol and 3-methyl-2-buten-1-ol) react with acyl isothiocyanates (4-chlorobenzoyl, 2,6-difluorobenzoyl, 3-phenylpropenoyl, 2-thienocarbonyl, 3-chloro-2-thienocarbonyl and 3-chloro-2-benzo[b]thienocarbonyl isothiocyanate) with the formation of highly reactive O-substituted allyl N-acylmonothiocarbamates, which either spontaneously or by heating in boiling benzene undergo [3,3]-sigmatropic rearrangement to S-substituted allyl N-acylmonothiocarbamates. The structure of S-esters with isomerized allylic group affords the unequivocal evidence of the [3,3]-sigmatropic route of studied rearrangement. Further heating of [3,3]-rearranged N-(4-chlorobenzoyl)monothiocarbamates results in the [1,3]-sigmatropic shift of monothiocarbamate group. Using arylalkyl alcohols with the allylic double bond inserted into an aromatic system the obtained O-esters either do not undergo any rearrangement (benzyl alcohol) or undergo [1,3]-sigmatropic rearrangement (2- and 3-furylmethanol and 1-(2-furyl)ethanol) to the corresponding S-esters. For explanation of this reaction the tandem of [3,3]- and [1,3]-sigmatropic rearrangements is suggested.

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2

Wang, Jialiang, Wen Huang, Zhengxing Zhang, Xu Xiang, Ruiting Liu i Xigeng Zhou. "FeCl3·6H2O Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol". Journal of Organic Chemistry 74, nr 9 (maj 2009): 3299–304. http://dx.doi.org/10.1021/jo900070q.

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3

Cooper, Matthew A., i A. David Ward. "Hydroxyselenation of allylic alcohols". Tetrahedron Letters 36, nr 13 (marzec 1995): 2327–30. http://dx.doi.org/10.1016/0040-4039(95)00247-a.

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4

Harada, Kohei, Marina Nogami, Keiichi Hirano, Daisuke Kurauchi, Hisano Kato, Kazunori Miyamoto, Tatsuo Saito i Masanobu Uchiyama. "Allylic borylation of tertiary allylic alcohols: a divergent and straightforward access to allylic boronates". Organic Chemistry Frontiers 3, nr 5 (2016): 565–69. http://dx.doi.org/10.1039/c6qo00009f.

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5

Chern, Ching-Yuh, Ching-Chun Tseng, Rong-Hong Hsiao, Fung Fuh Wong i Yueh-Hsiung Kuo. "Cyclopentadienyl Ruthenium(II) Complex-Mediated Oxidation of Benzylic and Allylic Alcohols to Corresponding Aldehydes". Heteroatom Chemistry 2019 (18.08.2019): 1–8. http://dx.doi.org/10.1155/2019/5053702.

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This work reports an efficient method for the oxidation reaction of aliphatic, aromatic allylic, and benzylic alcohols into aldehydes catalyzed by the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) with bubbled O2. Through further optimizing controlled studies, the tendency order of oxidation reactivity was determined as follows: benzylic alcohols > aromatic allylic alcohols >> aliphatic alcohols. In addition, this method has several advantages, including a small amount of catalyst (0.5 mol%) and selective application of high discrimination activity of aliphatic, aromatic allylic, and benzylic alcohols.

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6

Akkarasamiyo, Sunisa, Somsak Ruchirawat, Poonsaksi Ploypradith i Joseph S. M. Samec. "Transition-Metal-Catalyzed Suzuki–Miyaura-Type Cross-Coupling Reactions of π-Activated Alcohols". Synthesis 52, nr 05 (7.01.2020): 645–59. http://dx.doi.org/10.1055/s-0039-1690740.

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The Suzuki–Miyaura reaction is one of the most powerful tools for the formation of carbon–carbon bonds in organic synthesis. The utilization of alcohols in this powerful reaction is a challenging task. This short review covers progress in the transition-metal-catalyzed Suzuki–Miyaura-type cross-coupling reaction of π-activated alcohol, such as aryl, benzylic, allylic, propargylic and allenic alcohols, between 2000 and June 2019.1 Introduction2 Suzuki–Miyaura Cross-Coupling Reactions of Aryl Alcohols2.1 One-Pot Reactions with Pre-activation of the C–O Bond2.1.1 Palladium Catalysis2.1.2 Nickel Catalysis2.2 Direct Activation of the C–O Bond2.2.1 Nickel Catalysis3 Suzuki–Miyaura-Type Cross-Coupling Reactions of Benzylic Alcohols4 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allylic Alcohols4.1 Rhodium Catalysis4.2 Palladium Catalysis4.3 Nickel Catalysis4.4 Stereospecific Reactions4.5 Stereoselective Reactions4.6 Domino Reactions5 Suzuki–Miyaura-Type Cross-Coupling Reactions of Propargylic Alcohols5.1 Palladium Catalysis5.2 Rhodium Catalysis6 Suzuki–Miyaura-Type Cross-Coupling Reactions of Allenic Alcohols6.1 Palladium Catalysis6.2 Rhodium Catalysis7 Conclusions

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7

Hamada, Yoko, Rio Matsunaga, Tomoko Kawasaki-Takasuka i Takashi Yamazaki. "Base-Mediated Claisen Rearrangement of CF3-Containing Bisallyl Ethers". Molecules 26, nr 14 (19.07.2021): 4365. http://dx.doi.org/10.3390/molecules26144365.

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We have previously clarified that the strongly electron-withdrawing CF3 group nicely affected the base-mediated proton shift of CF3-containing propargylic or allylic alcohols to afford the corresponding α,β-unsaturated or saturated ketones, respectively, which was applied this time to the Claisen rearrangement after O-allylation of the allylic alcohols with a CF3 group, followed by isomerization to the corresponding allyl vinyl ethers via the proton shift, enabling the desired rearrangement in a tandem fashion, or in a stepwise manner, the latter of which was proved to have attained an excellent diastereoselectivity with the aid of a palladium catalyst.

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8

Jun, Chul-Ho, i Chang-Hee Lee. "Chelation-Assisted C–H and C–C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation". Synlett 29, nr 06 (16.11.2017): 736–41. http://dx.doi.org/10.1055/s-0036-1591697.

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Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C–H and C–C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C–H and C–C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

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9

Emayavaramban, Balakumar, Moumita Roy i Basker Sundararaju. "Iron-Catalyzed Allylic Amination Directly from Allylic Alcohols". Chemistry - A European Journal 22, nr 12 (17.02.2016): 3952–55. http://dx.doi.org/10.1002/chem.201505214.

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10

Berger, Anna Lucia, Karsten Donabauer i Burkhard König. "Photocatalytic Barbier reaction – visible-light induced allylation and benzylation of aldehydes and ketones". Chemical Science 9, nr 36 (2018): 7230–35. http://dx.doi.org/10.1039/c8sc02038h.

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We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols.

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11

Parisotto, Stefano, i Annamaria Deagostino. "π-Allylpalladium Complexes in Synthesis: An Update". Synthesis 51, nr 09 (20.03.2019): 1892–912. http://dx.doi.org/10.1055/s-0037-1611745.

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This review aims to summarize the development of the chemistry of π-allylpalladium complexes both as intermediates and catalysts/reagents between 2013 and early 2109. Major attention has been devoted to the synthetic aspect of these versatile intermediates.1 Introduction2 π-Allylpalladium Complexes Generated from Allyl Electrophiles2.1 Activated Allylic Compounds2.2 Unactivated Allylic Compounds: Allylic Alcohols and Hydrocarbons2.3 Total Syntheses3 π-Allylpalladium Complexes Generated from Dienes3.1 Conjugated Dienes3.2 Allenes4 π-Allylpalladium Complexes Exploited as Reactants and Precatalysts4.1 Allylpalladium-Catalyzed Dehydrogenation4.2 Allylpalladium-Catalyzed Synthesis of Alkenylboronic Esters4.3 Allylpalladium-Based Precatalysts5 Conclusions

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12

Jing, Jiangyan, Xiaohong Huo, Jiefeng Shen, Jingke Fu, Qinghua Meng i Wanbin Zhang. "Direct use of allylic alcohols and allylic amines in palladium-catalyzed allylic amination". Chemical Communications 53, nr 37 (2017): 5151–54. http://dx.doi.org/10.1039/c7cc01069a.

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Allylic alcohols and allylic amines were directly utilized in a Pd-catalyzed hydrogen-bond-activated allylic amination under mild reaction conditions in the absence of any additives. The catalytic system is compatible with a variety of functional groups and can be used to prepare a wide range of linear allylic amines in good to excellent yields.

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13

Masuyama, Yoshiro, Jun P. Takahara i Yasuhiko Kurusu. "Allylic alcohols as synthons of allylic carbanions. Palladium-catalyzed carbonyl allylation by allylic alcohols with tin dichloride". Journal of the American Chemical Society 110, nr 13 (czerwiec 1988): 4473–74. http://dx.doi.org/10.1021/ja00221a091.

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14

Kang, Ye-Won, i Hye-Young Jang. "NHC-catalyzed one-pot oxidation and oxidative esterification of allylic alcohols using TEMPO: the effect of alcohol additives". RSC Adv. 4, nr 84 (2014): 44486–90. http://dx.doi.org/10.1039/c4ra08133a.

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15

McLaughlin, Mark G., i Matthew J. Cook. "Highly diastereoselective hydrosilylations of allylic alcohols". Chem. Commun. 50, nr 26 (2014): 3501–4. http://dx.doi.org/10.1039/c4cc00138a.

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16

Luna, Hector, Kapa Prasad i Oljan Repič. "Microbial Oxidation of Allylic Alcohols". Biocatalysis 8, nr 2 (styczeń 1993): 155–62. http://dx.doi.org/10.3109/10242429308998202.

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17

Mohamadi, Fariborz, i W. Clark Still. "Dichlorocarbene cyclopropanation of allylic alcohols". Tetrahedron Letters 27, nr 8 (styczeń 1986): 893–96. http://dx.doi.org/10.1016/s0040-4039(00)84130-1.

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18

Cahard, Dominique, Sylvain Gaillard i Jean-Luc Renaud. "Asymmetric isomerization of allylic alcohols". Tetrahedron Letters 56, nr 45 (listopad 2015): 6159–69. http://dx.doi.org/10.1016/j.tetlet.2015.09.098.

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19

Levine, S. G., i N. E. Heard. "Chemical Resolution of Allylic Alcohols". Synthetic Communications 21, nr 4 (luty 1991): 549–55. http://dx.doi.org/10.1080/00397919108016782.

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20

Lightburn, Thomas E., Omar A. De Paolis, Ka H. Cheng i Kian L. Tan. "Regioselective Hydroformylation of Allylic Alcohols". Organic Letters 13, nr 10 (20.05.2011): 2686–89. http://dx.doi.org/10.1021/ol200782d.

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21

Shinde, Anand H., i Shyam Sathyamoorthi. "Tethered Silanoxymercuration of Allylic Alcohols". Organic Letters 22, nr 21 (23.10.2020): 8665–69. http://dx.doi.org/10.1021/acs.orglett.0c03257.

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22

Nicolaou, K. C., Nicholas L. Simmons, Yongcheng Ying, Philipp M. Heretsch i Jason S. Chen. "Enantioselective Dichlorination of Allylic Alcohols". Journal of the American Chemical Society 133, nr 21 (czerwiec 2011): 8134–37. http://dx.doi.org/10.1021/ja202555m.

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23

Carreira, E., i M. Roggen. "Stereospecific Substitution of Allylic Alcohols". Synfacts 2010, nr 11 (21.10.2010): 1259. http://dx.doi.org/10.1055/s-0030-1258797.

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24

Xu, Jing-Kun, Yonghong Gu i Shi-Kai Tian. "Enantiospecific Allylic Alkylation of Substituted Hydrazines with Allylic Alcohols". Chinese Journal of Organic Chemistry 35, nr 3 (2015): 618. http://dx.doi.org/10.6023/cjoc201412049.

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25

Chan, Philip, Xiaoxiang Zhang i Weidong Rao. "Iodine-Catalyzed Allylic Alkylation of Thiols with Allylic Alcohols". Synlett 2008, nr 14 (sierpień 2008): 2204–8. http://dx.doi.org/10.1055/s-2008-1078254.

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26

Ying, Xiangxian, Yifang Wang, Bin Xiong, Tingting Wu, Liping Xie, Meilan Yu i Zhao Wang. "Characterization of an Allylic/Benzyl Alcohol Dehydrogenase from Yokenella sp. Strain WZY002, an Organism Potentially Useful for the Synthesis of α,β-Unsaturated Alcohols from Allylic Aldehydes and Ketones". Applied and Environmental Microbiology 80, nr 8 (7.02.2014): 2399–409. http://dx.doi.org/10.1128/aem.03980-13.

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ABSTRACTA novel whole-cell biocatalyst with high allylic alcohol-oxidizing activities was screened and identified asYokenellasp. WZY002, which chemoselectively reduced the C=O bond of allylic aldehydes/ketones to the corresponding α,β-unsaturated alcohols at 30°C and pH 8.0. The strain also had the capacity of stereoselectively reducing aromatic ketones to (S)-enantioselective alcohols. The enzyme responsible for the predominant allylic/benzyl alcohol dehydrogenase activity was purified to homogeneity and designated YsADH (alcohol dehydrogenase fromYokenellasp.), which had a calculated subunit molecular mass of 36,411 Da. The gene encoding YsADH was subsequently expressed inEscherichia coli, and the purified recombinant YsADH protein was characterized. The enzyme strictly required NADP(H) as a coenzyme and was putatively zinc dependent. The optimal pH and temperature for crotonaldehyde reduction were pH 6.5 and 65°C, whereas those for crotyl alcohol oxidation were pH 8.0 and 55°C. The enzyme showed moderate thermostability, with a half-life of 6.2 h at 55°C. It was robust in the presence of organic solvents and retained 87.5% of the initial activity after 24 h of incubation with 20% (vol/vol) dimethyl sulfoxide. The enzyme preferentially catalyzed allylic/benzyl aldehydes as the substrate in the reduction of aldehydes/ketones and yielded the highest activity of 427 U mg−1for benzaldehyde reduction, while the alcohol oxidation reaction demonstrated the maximum activity of 79.9 U mg−1using crotyl alcohol as the substrate. Moreover, kinetic parameters of the enzyme showed lowerKmvalues and higher catalytic efficiency for crotonaldehyde/benzaldehyde and NADPH than for crotyl alcohol/benzyl alcohol and NADP+, suggesting the nature of being an aldehyde reductase.

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27

Qi, Juan, Guo-Tao Fan, Jie Chen, Ming-Hui Sun, Yu-Ting Dong i Ling Zhou. "Catalytic enantioselective bromoamination of allylic alcohols". Chem. Commun. 50, nr 89 (2014): 13841–44. http://dx.doi.org/10.1039/c4cc05772d.

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28

Guo, Guozhe, Yong Yuan, Shuocheng Wan, Xuehui Cao, Yali Sun i Congde Huo. "K2S2O8 promoted dehydrative cross-coupling between α,α-disubstituted allylic alcohols and thiophenols/thiols". Organic Chemistry Frontiers 8, nr 12 (2021): 2990–96. http://dx.doi.org/10.1039/d1qo00148e.

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K₂S₂O₈ promoted dehydrative cross-coupling between α,α-disubstituted allylic alcohols and thiophenols/thiols is demonstrated for the first time, leading to a wide range of allyl sulfides in good to high yields.

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29

Discordia, Robert P., Christopher K. Murphy i Donald C. Dittmer. "Telluride-mediated stereospecific conversion of racemic E-allylic alcohols to homochiral Z-allylic alcohols; transposition of primary and secondary allylic alcohols via glycidol derivatives". Tetrahedron Letters 31, nr 39 (1990): 5603–6. http://dx.doi.org/10.1016/s0040-4039(00)97907-3.

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30

Cai, Mingzhong, Chunyun Peng, Hong Zhao i Wenyan Hao. "A Stereoselective Synthesis of (E)-Allylic Alcohols Via the Hydromagnesiation of Alkynylsilanes". Journal of Chemical Research 2003, nr 5 (maj 2003): 296–98. http://dx.doi.org/10.3184/030823403103173877.

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Hydromagnesiation of alkynylsilanes 1 gives ( Z)-α-silylvinyl Grignard reagents 2, which are reacted with aldehydes or ketones to afford ( Z)-β-silyl allylic alcohols 3 in high yields; intermediates 3 can undergo the desilylation reaction in the presence of anhydrous KF to give ( E)-allylic alcohols 4 in good yields.

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31

Xu, Ruigang, Kai Li, Jiaqi Wang, Jiamin Lu, Lina Pan, Xiaofei Zeng i Guofu Zhong. "Direct enantioselective allylic substitution of 4-hydroxycoumarin derivatives with branched allylic alcohols via iridium catalysis". Chemical Communications 56, nr 60 (2020): 8404–7. http://dx.doi.org/10.1039/d0cc02832k.

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An iridium catalysed direct asymmetric allylic substitution reaction of 4-hydroxycoumarin derivatives with allylic alcohols with remarkably high yields and excellent enantioselectivities was realized.

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32

Prieto, Consuelo, José A. González Delgado, Jesús F. Arteaga, Martín Jaraíz, José L. López-Pérez i Alejandro F. Barrero. "Homocoupling versus reduction of radicals: an experimental and theoretical study of Ti(iii)-mediated deoxygenation of activated alcohols". Organic & Biomolecular Chemistry 13, nr 11 (2015): 3462–69. http://dx.doi.org/10.1039/c4ob02290d.

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A detailed study corroborates that the Ti(iii)-mediated reductive deoxygenation of activated -OH proceeds via an allyl(benzyl)-radical and allyl(benzyl)-Ti, which is protonated, regioselectively in the case of allylic derivatives.

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33

Abad, Alberto, Avelino Corma i Hermenegildo García. "Supported gold nanoparticles for aerobic, solventless oxidation of allylic alcohols". Pure and Applied Chemistry 79, nr 11 (1.01.2007): 1847–54. http://dx.doi.org/10.1351/pac200779111847.

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After giving some general considerations about the specific properties of nanoparticles below 20 nm, procedures for size stabilization, and the importance of developing green alcohol oxidation reactions, catalytic data are presented showing that gold nanoparticles (3-7 nm) supported on nanoparticulated ceria (4 nm) are far more chemoselective than related palladium catalysts for the aerobic oxidation of allylic alcohols. Using palladium catalysts, in addition to minor oxidation of the alcohol functional group, we have also observed polymerization, 1-2 hydrogen shift, and hydrogenation. In contrast, ceria-supported gold nanoparticles exhibit a remarkable chemoselectivity (in many cases, almost complete) to the alcohol oxidation.

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34

Dorta, Rosa L., María S. Rodríguez, JoséA Salazar i Ernesto Suárez. "1,3-Transposition of primary allylic alcohols: Synthesis of optically active secondary and tertiary allylic alcohols". Tetrahedron Letters 38, nr 26 (czerwiec 1997): 4675–78. http://dx.doi.org/10.1016/s0040-4039(97)00964-7.

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35

Guo, Yunlong, i Zengming Shen. "Palladium-catalyzed allylic C–H oxidation under simple operation and mild conditions". Organic & Biomolecular Chemistry 17, nr 12 (2019): 3103–7. http://dx.doi.org/10.1039/c9ob00209j.

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36

Xie, Peizhong, Zuolian Sun, Shuangshuang Li, Xinying Cai, Ju Qiu, Weishan Fu, Cuiqing Gao, Shisheng Wu, Xiaobo Yang i Teck-Peng Loh. "Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols". Organic Letters 22, nr 12 (4.06.2020): 4893–97. http://dx.doi.org/10.1021/acs.orglett.0c01747.

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37

Lafrance, Marc, Markus Roggen i Erick M. Carreira. "Direct, Enantioselective Iridium-Catalyzed Allylic Amination of Racemic Allylic Alcohols". Angewandte Chemie International Edition 51, nr 14 (17.02.2012): 3470–73. http://dx.doi.org/10.1002/anie.201108287.

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38

Carreira, E., C. Defieber, M. Ariger i P. Moriel. "Iridium-Catalyzed Synthesis of Primary Allylic Amines from Allylic Alcohols". Synfacts 2007, nr 7 (lipiec 2007): 0731. http://dx.doi.org/10.1055/s-2007-968662.

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39

Ma, Xinghua, Natasha Anderson, Lorenzo V. White, Song Bae, Warwick Raverty, Anthony C. Willis i Martin G. Banwell. "The Conversion of Levoglucosenone into Isolevoglucosenone". Australian Journal of Chemistry 68, nr 4 (2015): 593. http://dx.doi.org/10.1071/ch14574.

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Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

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40

Liang, Xiao, Kun Wei i Yu-Rong Yang. "Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones". Chemical Communications 51, nr 98 (2015): 17471–74. http://dx.doi.org/10.1039/c5cc07221b.

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41

Li, Hongfang, Tao Li, Yu Jen Hsueh, Xue Wu, Feng Xu i Yong Jian Zhang. "Tandem arylation and regioselective allylic etherification of 2,3-allenol via Pd/B cooperative catalysis". Organic & Biomolecular Chemistry 17, nr 35 (2019): 8075–78. http://dx.doi.org/10.1039/c9ob01792e.

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42

Antonioletti, R., F. Bonadies, L. Locati i A. Scettri. "Zeolite-catalyzed epoxidation of allylic alcohols". Tetrahedron Letters 33, nr 22 (maj 1992): 3205–6. http://dx.doi.org/10.1016/s0040-4039(00)79852-2.

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43

Donohoe, Timothy J., Peter R. Moore, Michael J. Waring i Nicholas J. Newcombe. "The directed dihydroxylation of allylic alcohols". Tetrahedron Letters 38, nr 28 (lipiec 1997): 5027–30. http://dx.doi.org/10.1016/s0040-4039(97)01061-7.

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44

Wang, Zhi-Min, i K. Barry Sharpless. "Asymmetric dihydroxylation of tertiary allylic alcohols". Tetrahedron Letters 34, nr 51 (grudzień 1993): 8225–28. http://dx.doi.org/10.1016/s0040-4039(00)61396-5.

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