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Journal articles on the topic 'Piancatelli'

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Author: Grafiati

Published: 20 July 2024

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1

Cai, Yunfei, Sishi Zhong, and Lei Xu. "Recent Advances on Piancatelli Reactions and Related Cascade Processes." Synthesis 54, no. 03 (November 15, 2021): 589–99. http://dx.doi.org/10.1055/s-0041-1737125.

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AbstractThe Piancatelli reaction, which is the rearrangement of 2-furylcarbinol to cyclopentenone, involves a key furanoxonium ion intermediate and a furan ring opening-4π electrocyclization process. In recent years, the original oxa-Piancatelli reaction has been extended to a large family of aza- and carbo-Piancatelli reactions and related cascade processes, providing a powerful platform for the construction of diverse functionalized cyclopentenones and polycyclic cyclopentanones. Meanwhile, chiral Brønsted/Lewis acid based catalytic asymmetric approaches to Piancatelli reactions have also been achieved for the assembly of highly valued chiral cyclopentenone scaffolds. In this short review, we present an overview of the recent developments in these areas and focus primarily on reports published in the last five years.1 Introduction2 Diastereoselective Oxa-, Aza- and Carbo-Piancatelli Reactions3 Diastereoselective Cascade Piancatelli Reactions4 Asymmetric Piancatelli Reactions and Related Cascade Processes5 Miscellaneous Furanoxonium Ion-Based Rearrangements6 Conclusion

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2

Zheng, Wen-Hua, Wu-Bang Tang, Kou-Sen Cao, and Shan-Shui Meng. "Boronic Acid Catalysis for Aza-Piancatelli Rearrangement." Synthesis 49, no. 16 (June 20, 2017): 3670–75. http://dx.doi.org/10.1055/s-0036-1589040.

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A first example of boronic acid catalyzed intermolecular aza-Piancatelli rearrangement to access a wide range of trans-4,5-disubstituted cyclopentenones is described. The catalytic system can also be extended to intramolecular aza-Piancatelli rearrangement to afford a wide range of azaspirocycles. Good to excellent yields were obtained in an excellent diastereoselective manner.

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3

Schober, Lukas, Makoto Sako, Shinobu Takizawa, Harald Gröger, and Hiroaki Sasai. "Catalytic and enantioselective oxa-Piancatelli reaction using a chiral vanadium complex." Chemical Communications 56, no. 70 (2020): 10151–54. http://dx.doi.org/10.1039/d0cc02621b.

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4

Patil, Nitin, and Amol Gade. "Catalytic Enantioselective Aza-Piancatelli Rearrangement." Synlett 28, no. 09 (February 13, 2017): 1096–100. http://dx.doi.org/10.1055/s-0036-1558952.

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5

Li, Huilin, Rongbiao Tong, and Jianwei Sun. "Catalytic Enantioselective Aza-Piancatelli Rearrangement." Angewandte Chemie International Edition 55, no. 48 (October 27, 2016): 15125–28. http://dx.doi.org/10.1002/anie.201607714.

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6

Li, Huilin, Rongbiao Tong, and Jianwei Sun. "Catalytic Enantioselective Aza-Piancatelli Rearrangement." Angewandte Chemie 128, no. 48 (October 27, 2016): 15349–52. http://dx.doi.org/10.1002/ange.201607714.

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7

Verrier, Charlie, Sylvie Moebs-Sanchez, Yves Queneau, and Florence Popowycz. "The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization." Organic & Biomolecular Chemistry 16, no. 5 (2018): 676–87. http://dx.doi.org/10.1039/c7ob02962d.

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8

Veits, Gesine K., Donald R. Wenz, Leoni I. Palmer, André H. St. Amant, Jason E. Hein, and Javier Read de Alaniz. "Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives." Organic & Biomolecular Chemistry 13, no. 31 (2015): 8465–69. http://dx.doi.org/10.1039/c5ob00944h.

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The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.

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9

Shen, Bin, Qianwen He, Shunxi Dong, Xiaohua Liu, and Xiaoming Feng. "A chiral cobalt(ii) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction." Chemical Science 11, no. 15 (2020): 3862–67. http://dx.doi.org/10.1039/d0sc00542h.

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An asymmetric aza-Piancatelli rearrangement/Diels–Alder cascade reaction between 2-furylcarbinols and N-(furan-2-ylmethyl)anilines was realized by using a chiral N,N′-dioxide/cobalt(ii) complex catalyst.

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10

Marin, Lucile, Soufyan Jerhaoui, Emilie Kolodziej, Régis Guillot, Vincent Gandon, Françoise Colobert, Emmanuelle Schulz, Joanna Wencel‐Delord, and David Lebœuf. "Sulfoxide‐Controlled Stereoselective Aza‐Piancatelli Reaction." Advanced Synthesis & Catalysis 363, no. 17 (July 29, 2021): 4277–82. http://dx.doi.org/10.1002/adsc.202100848.

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11

Lebœuf, David, Emmanuelle Schulz, and Vincent Gandon. "Calcium(II)-Catalyzed Aza-Piancatelli Reaction." Organic Letters 16, no. 24 (December 8, 2014): 6464–67. http://dx.doi.org/10.1021/ol5032987.

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12

Hammersley, Gabrielle R., Meghan F. Nichol, Helena C. Steffens, Jose M. Delgado, Gesine K. Veits, and Javier Read de Alaniz. "Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement." Beilstein Journal of Organic Chemistry 15 (July 12, 2019): 1569–74. http://dx.doi.org/10.3762/bjoc.15.160.

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An enantioselective aza-Piancatelli rearrangement has been developed using a chiral Brønsted acid based on pentacarboxycyclopentadiene (PCCP). This reaction provides rapid access to valuable chiral 4-amino-2-cyclopentenone building blocks from readily available starting material and is operationally simple.

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13

Palmer, L., and J. Read de Alaniz. "Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Synfacts 2011, no. 11 (October 19, 2011): 1264. http://dx.doi.org/10.1055/s-0031-1289300.

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14

Subba Reddy, B. V., Y. Vikram Reddy, and Kiran Kumar Singarapu. "Sequential aza-Piancatelli rearrangement/Friedel–Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives." Organic & Biomolecular Chemistry 14, no. 3 (2016): 1111–16. http://dx.doi.org/10.1039/c5ob01616a.

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2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel–Crafts alkylation with (1H-pyrrol-1-yl)aniline, in the presence of In(OTf)₃ at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds.

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15

Leboeuf, David, Emmanuelle Schulz, and Vincent Gandon. "ChemInform Abstract: Calcium(II)-Catalyzed Aza-Piancatelli Reaction." ChemInform 46, no. 21 (May 2015): no. http://dx.doi.org/10.1002/chin.201521059.

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16

Piutti, Claudia, and Francesca Quartieri. "The Piancatelli Rearrangement: New Applications for an Intriguing Reaction." Molecules 18, no. 10 (October 8, 2013): 12290–312. http://dx.doi.org/10.3390/molecules181012290.

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17

Xu, Lei, Sishi Zhong, Qian Yang, Jie Wei, Jiaming Zou, Hongxiang Li, and Yunfei Cai. "Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type Rearrangement of Furylalkenes." ACS Catalysis 11, no. 16 (August 2, 2021): 10198–207. http://dx.doi.org/10.1021/acscatal.1c03119.

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18

Fisher, David, Leoni I. Palmer, Jonathan E. Cook, Jessica E. Davis, and Javier Read de Alaniz. "Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangement." Tetrahedron 70, no. 27-28 (July 2014): 4105–10. http://dx.doi.org/10.1016/j.tet.2014.03.007.

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19

Nichol, Meghan. "Preparation of Cyclopent-2-enone Derivatives via the Aza-Piancatelli Rearrangement." Organic Syntheses 95 (2018): 46–59. http://dx.doi.org/10.15227/orgsyn.095.0046.

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20

Wenz, Donald R., and Javier Read de Alaniz. "Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor–Acceptor Cyclopropanes." Organic Letters 15, no. 13 (June 17, 2013): 3250–53. http://dx.doi.org/10.1021/ol401248p.

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21

Piutti, Claudia, and Francesca Quartieri. "ChemInform Abstract: The Piancatelli Rearrangement: New Applications for an Intriguing Reaction." ChemInform 45, no. 23 (May 22, 2014): no. http://dx.doi.org/10.1002/chin.201423272.

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22

Yu, Diana, Van T. Thai, Leoni I. Palmer, Gesine K. Veits, Jonathan E. Cook, Javier Read de Alaniz, and Jason E. Hein. "Importance of Off-Cycle Species in the Acid-Catalyzed Aza-Piancatelli Rearrangement." Journal of Organic Chemistry 78, no. 24 (December 11, 2013): 12784–89. http://dx.doi.org/10.1021/jo402155b.

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23

Palmer, Leoni I., and Javier Read de Alaniz. "Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement." Organic Letters 15, no. 3 (January 23, 2013): 476–79. http://dx.doi.org/10.1021/ol303263q.

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24

Xu, Zhong-Li, Ping Xing, and Biao Jiang. "Intramolecular Aza-Piancatelli Rearrangement of Alkyl- or Arylamines Promoted by PPh3/Diethyl Azodicarboxylate." Organic Letters 19, no. 5 (February 16, 2017): 1028–31. http://dx.doi.org/10.1021/acs.orglett.6b03853.

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25

Read de Alaniz, Javier, and Leoni Palmer. "Lewis Acid Catalyzed Rearrangement of Furylcarbinols: The Aza- and Oxa-Piancatelli Cascade Reaction." Synlett 25, no. 01 (November 6, 2013): 08–11. http://dx.doi.org/10.1055/s-0033-1340157.

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26

Wenz, Donald R., and Javier Read de Alaniz. "ChemInform Abstract: Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor-Acceptor Cyclopropanes." ChemInform 44, no. 48 (November 8, 2013): no. http://dx.doi.org/10.1002/chin.201348061.

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27

Fisher, David, Leoni I. Palmer, Jonathan E. Cook, Jessica E. Davis, and Javier Read de Alaniz. "ChemInform Abstract: Efficient Synthesis of 4-Hydroxycyclopentenones: Dysprosium(III) Triflate Catalyzed Piancatelli Rearrangement." ChemInform 45, no. 44 (October 16, 2014): no. http://dx.doi.org/10.1002/chin.201444058.

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28

Huang, Li, Xiaoyu Zhang, Jing Li, Ke Ding, Xuehui Li, Wenxu Zheng, and Biaolin Yin. "Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a StepwiseC-Piancatelli Rearrangement." European Journal of Organic Chemistry 2014, no. 2 (November 15, 2013): 338–49. http://dx.doi.org/10.1002/ejoc.201301238.

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29

Palmer, Leoni I., and Javier Read de Alaniz. "ChemInform Abstract: Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement." ChemInform 44, no. 24 (May 23, 2013): no. http://dx.doi.org/10.1002/chin.201324078.

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30

Cai, Yunfei, Yurong Tang, Iuliana Atodiresei, and Magnus Rueping. "Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones." Angewandte Chemie International Edition 55, no. 45 (October 10, 2016): 14126–30. http://dx.doi.org/10.1002/anie.201608023.

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31

Palmer, Leoni I., and Javier Read de Alaniz. "ChemInform Abstract: Lewis Acid Catalyzed Rearrangement of Furylcarbinols: The Aza- and Oxa-Piancatelli Cascade Reaction." ChemInform 45, no. 25 (June 5, 2014): no. http://dx.doi.org/10.1002/chin.201425067.

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32

Veits, Gesine K., Donald R. Wenz, and Javier Read de Alaniz. "Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Angewandte Chemie International Edition 49, no. 49 (November 4, 2010): 9484–87. http://dx.doi.org/10.1002/anie.201005131.

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33

Cai, Yunfei, Yurong Tang, Iuliana Atodiresei, and Magnus Rueping. "Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones." Angewandte Chemie 128, no. 45 (October 10, 2016): 14332–36. http://dx.doi.org/10.1002/ange.201608023.

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34

Veits, Gesine K., Donald R. Wenz, and Javier Read de Alaniz. "Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Angewandte Chemie 122, no. 49 (November 4, 2010): 9674–77. http://dx.doi.org/10.1002/ange.201005131.

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35

Xu, Jianfeng, Yi Luo, Huaping Xu, Zhengkai Chen, Maozhong Miao, and Hongjun Ren. "Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction." Journal of Organic Chemistry 82, no. 7 (March 9, 2017): 3561–70. http://dx.doi.org/10.1021/acs.joc.7b00090.

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36

Gutnov, Andrey V., Vladimir T. Abaev, and Oleg P. Demidov. "Betti reaction of 2-naphthol, furfural, and acetamide: an unexpected case of secondary carbo-Piancatelli rearrangement." Chemistry of Heterocyclic Compounds 55, no. 3 (March 2019): 280–82. http://dx.doi.org/10.1007/s10593-019-02454-0.

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37

Wang, Shengdong, Régis Guillot, Jean‐François Carpentier, Yann Sarazin, Christophe Bour, Vincent Gandon, and David Lebœuf. "Synthesis of Bridged Tetrahydrobenzo[ b ]azepines and Derivatives through an Aza‐Piancatelli Cyclization/Michael Addition Sequence." Angewandte Chemie International Edition 59, no. 3 (November 27, 2019): 1134–38. http://dx.doi.org/10.1002/anie.201911761.

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38

Palmer, Leoni I., and Javier Read de Alaniz. "Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Angewandte Chemie International Edition 50, no. 31 (June 17, 2011): 7167–70. http://dx.doi.org/10.1002/anie.201102102.

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39

Wang, Shengdong, Régis Guillot, Jean‐François Carpentier, Yann Sarazin, Christophe Bour, Vincent Gandon, and David Lebœuf. "Synthesis of Bridged Tetrahydrobenzo[ b ]azepines and Derivatives through an Aza‐Piancatelli Cyclization/Michael Addition Sequence." Angewandte Chemie 132, no. 3 (November 27, 2019): 1150–54. http://dx.doi.org/10.1002/ange.201911761.

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40

Palmer, Leoni I., and Javier Read de Alaniz. "Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Angewandte Chemie 123, no. 31 (June 17, 2011): 7305–8. http://dx.doi.org/10.1002/ange.201102102.

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41

Gouse, Shaik, Narra Rajashekar Reddy, and Sundarababu Baskaran. "A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels–Alder Reaction: Stereoselective Synthesis of Octahydro-1H-cyclopenta[cd]isoindole." Organic Letters 21, no. 10 (May 8, 2019): 3822–27. http://dx.doi.org/10.1021/acs.orglett.9b01267.

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42

Chung, Ryan, Diana Yu, Van T. Thai, Alyssa F. Jones, Gesine K. Veits, Javier Read de Alaniz, and Jason E. Hein. "Tandem Reaction Progress Analysis as a Means for Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement." ACS Catalysis 5, no. 8 (June 30, 2015): 4579–85. http://dx.doi.org/10.1021/acscatal.5b01087.

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43

Xu, Lei, Qian Yang, Sishi Zhong, Hongxiang Li, Yurong Tang, and Yunfei Cai. "Ln(III)/Chiral Brønsted Acid Catalyzed Asymmetric Cascade Ring Opening/Aza-Piancatelli Rearrangement of D–A Cyclopropanes." Organic Letters 22, no. 22 (November 10, 2020): 9016–21. http://dx.doi.org/10.1021/acs.orglett.0c03413.

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44

González-Pérez, Adán B., Pedro Villar, and Angel R. de Lera. "A Computational Study of Model Parent Systems and Reported Aza-(Iso)Nazarov/Aza-(Iso)Piancatelli Electrocyclic Reactions." European Journal of Organic Chemistry 2019, no. 14 (April 5, 2019): 2539–51. http://dx.doi.org/10.1002/ejoc.201900103.

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45

Veits, Gesine K., Donald R. Wenz, and Javier Read de Alaniz. "ChemInform Abstract: Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium (III) Triflate Catalyzed Aza-Piancatelli Rearrangement." ChemInform 42, no. 15 (March 17, 2011): no. http://dx.doi.org/10.1002/chin.201115064.

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46

Huang, Li, Xiaoyu Zhang, Jing Li, Ke Ding, Xuehui Li, Wenxu Zheng, and Biaolin Yin. "ChemInform Abstract: Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a Stepwise C-Piancatelli Rearrangement." ChemInform 45, no. 43 (October 10, 2014): no. http://dx.doi.org/10.1002/chin.201443083.

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47

Nayani, Kiranmai, Radhika Cinsani, Anwar Hussaini SD, Prathama S. Mainkar, and Srivari Chandrasekhar. "Brønsted Acid Catalyzed Domino Aza-Piancatelli Rearrangement/Michael Reaction: Construction of 1,4-Benzodiazepin-5-ones in One Pot." European Journal of Organic Chemistry 2017, no. 37 (October 9, 2017): 5671–78. http://dx.doi.org/10.1002/ejoc.201700957.

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48

Palmer, Leoni I., and Javier Read de Alaniz. "ChemInform Abstract: Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." ChemInform 42, no. 51 (November 24, 2011): no. http://dx.doi.org/10.1002/chin.201151090.

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49

Orozco-Saumell, Ana, Rafael Mariscal, Francisco Vila, Manuel López Granados, and David Martín Alonso. "Hydrogenation of Furfural to Cyclopentanone in Tert–Butanol-Water Medium: A Study of the Reaction Intermediates Reactivity Using Cu/ZnO/Al2O3 as Catalyst." Catalysts 13, no. 11 (October 25, 2023): 1394. http://dx.doi.org/10.3390/catal13111394.

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The catalytic transformation of furfural to cyclopentanone has been investigated using two different liquid phases as solvent: water and 30 wt.% tert–butanol in water. When using neat water at 160 °C, 40 bar of H2, and after 2 h of reaction time, furfural polymerizes, and the yield of cyclopentanone is just 42% with a low carbon balance, indicating that furfural is transformed to non-detected by-products, likely heavy resins. When using 30 wt.% tert–butanol in water, the yield of cyclopentanone is ca. 20%, and the major product is furfuryl alcohol with a 47% yield. We have studied the catalytic transformation of the most relevant reaction intermediates in the overall conversion of furfural to cyclopentanone. In the presence of tert–butanol, two steps are inhibited in the overall pathway: (i) the Piancatelli rearrangement of furfuryl alcohol and (ii) the transformation of cyclopentenone. This inhibition is attributed to the neutralization of protons from water dissociation by surface sites on the catalyst, preventing their participation in the overall reaction. To counteract these inhibitions when tert–butanol is present, higher H2 pressure (60 bar) and temperatures (200 °C) are required. We have been able to obtain productivities per gram of catalyst and mols of Cu basis of 411 gprod·h−1·gcat−1 and 14 gprod·s−1·molCu−1, respectively, which is substantially above that found for other copper-based catalysts.

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50

Lebœuf, David, Lucile Marin, Bastien Michelet, Alejandro Perez-Luna, Régis Guillot, Emmanuelle Schulz, and Vincent Gandon. "Harnessing the Lewis Acidity of HFIP through its Cooperation with a Calcium(II) Salt: Application to the Aza-Piancatelli Reaction." Chemistry - A European Journal 22, no. 45 (September 30, 2016): 16165–71. http://dx.doi.org/10.1002/chem.201603592.

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