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Artykuły w czasopismach na temat „Piancatelli”

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Data publikacji: 20 lipca 2024

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1

Cai, Yunfei, Sishi Zhong i Lei Xu. "Recent Advances on Piancatelli Reactions and Related Cascade Processes". Synthesis 54, nr 03 (15.11.2021): 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 i Shan-Shui Meng. "Boronic Acid Catalysis for Aza-Piancatelli Rearrangement". Synthesis 49, nr 16 (20.06.2017): 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 i Hiroaki Sasai. "Catalytic and enantioselective oxa-Piancatelli reaction using a chiral vanadium complex". Chemical Communications 56, nr 70 (2020): 10151–54. http://dx.doi.org/10.1039/d0cc02621b.

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4

Patil, Nitin, i Amol Gade. "Catalytic Enantioselective Aza-Piancatelli Rearrangement". Synlett 28, nr 09 (13.02.2017): 1096–100. http://dx.doi.org/10.1055/s-0036-1558952.

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5

Li, Huilin, Rongbiao Tong i Jianwei Sun. "Catalytic Enantioselective Aza-Piancatelli Rearrangement". Angewandte Chemie International Edition 55, nr 48 (27.10.2016): 15125–28. http://dx.doi.org/10.1002/anie.201607714.

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6

Li, Huilin, Rongbiao Tong i Jianwei Sun. "Catalytic Enantioselective Aza-Piancatelli Rearrangement". Angewandte Chemie 128, nr 48 (27.10.2016): 15349–52. http://dx.doi.org/10.1002/ange.201607714.

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7

Verrier, Charlie, Sylvie Moebs-Sanchez, Yves Queneau i Florence Popowycz. "The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization". Organic & Biomolecular Chemistry 16, nr 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 i Javier Read de Alaniz. "Cascade rearrangement of furylcarbinols with hydroxylamines: practical access to densely functionalized cyclopentane derivatives". Organic & Biomolecular Chemistry 13, nr 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 i Xiaoming Feng. "A chiral cobalt(ii) complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels–Alder cascade reaction". Chemical Science 11, nr 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 i David Lebœuf. "Sulfoxide‐Controlled Stereoselective Aza‐Piancatelli Reaction". Advanced Synthesis & Catalysis 363, nr 17 (29.07.2021): 4277–82. http://dx.doi.org/10.1002/adsc.202100848.

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11

Lebœuf, David, Emmanuelle Schulz i Vincent Gandon. "Calcium(II)-Catalyzed Aza-Piancatelli Reaction". Organic Letters 16, nr 24 (8.12.2014): 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 i Javier Read de Alaniz. "Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement". Beilstein Journal of Organic Chemistry 15 (12.07.2019): 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., i J. Read de Alaniz. "Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement". Synfacts 2011, nr 11 (19.10.2011): 1264. http://dx.doi.org/10.1055/s-0031-1289300.

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14

Subba Reddy, B. V., Y. Vikram Reddy i Kiran Kumar Singarapu. "Sequential aza-Piancatelli rearrangement/Friedel–Crafts alkylation for the synthesis of pyrrolo[1,2-d]benzodiazepine derivatives". Organic & Biomolecular Chemistry 14, nr 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 i Vincent Gandon. "ChemInform Abstract: Calcium(II)-Catalyzed Aza-Piancatelli Reaction." ChemInform 46, nr 21 (maj 2015): no. http://dx.doi.org/10.1002/chin.201521059.

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16

Piutti, Claudia, i Francesca Quartieri. "The Piancatelli Rearrangement: New Applications for an Intriguing Reaction". Molecules 18, nr 10 (8.10.2013): 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 i Yunfei Cai. "Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type Rearrangement of Furylalkenes". ACS Catalysis 11, nr 16 (2.08.2021): 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 i Javier Read de Alaniz. "Efficient synthesis of 4-hydroxycyclopentenones: dysprosium(III) triflate catalyzed Piancatelli rearrangement". Tetrahedron 70, nr 27-28 (lipiec 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., i Javier Read de Alaniz. "Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor–Acceptor Cyclopropanes". Organic Letters 15, nr 13 (17.06.2013): 3250–53. http://dx.doi.org/10.1021/ol401248p.

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21

Piutti, Claudia, i Francesca Quartieri. "ChemInform Abstract: The Piancatelli Rearrangement: New Applications for an Intriguing Reaction". ChemInform 45, nr 23 (22.05.2014): 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 i Jason E. Hein. "Importance of Off-Cycle Species in the Acid-Catalyzed Aza-Piancatelli Rearrangement". Journal of Organic Chemistry 78, nr 24 (11.12.2013): 12784–89. http://dx.doi.org/10.1021/jo402155b.

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23

Palmer, Leoni I., i Javier Read de Alaniz. "Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement". Organic Letters 15, nr 3 (23.01.2013): 476–79. http://dx.doi.org/10.1021/ol303263q.

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24

Xu, Zhong-Li, Ping Xing i Biao Jiang. "Intramolecular Aza-Piancatelli Rearrangement of Alkyl- or Arylamines Promoted by PPh3/Diethyl Azodicarboxylate". Organic Letters 19, nr 5 (16.02.2017): 1028–31. http://dx.doi.org/10.1021/acs.orglett.6b03853.

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25

Read de Alaniz, Javier, i Leoni Palmer. "Lewis Acid Catalyzed Rearrangement of Furylcarbinols: The Aza- and Oxa-Piancatelli Cascade Reaction". Synlett 25, nr 01 (6.11.2013): 08–11. http://dx.doi.org/10.1055/s-0033-1340157.

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26

Wenz, Donald R., i Javier Read de Alaniz. "ChemInform Abstract: Aza-Piancatelli Rearrangement Initiated by Ring Opening of Donor-Acceptor Cyclopropanes." ChemInform 44, nr 48 (8.11.2013): 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 i Javier Read de Alaniz. "ChemInform Abstract: Efficient Synthesis of 4-Hydroxycyclopentenones: Dysprosium(III) Triflate Catalyzed Piancatelli Rearrangement." ChemInform 45, nr 44 (16.10.2014): 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 i Biaolin Yin. "Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a StepwiseC-Piancatelli Rearrangement". European Journal of Organic Chemistry 2014, nr 2 (15.11.2013): 338–49. http://dx.doi.org/10.1002/ejoc.201301238.

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29

Palmer, Leoni I., i Javier Read de Alaniz. "ChemInform Abstract: Rapid and Stereoselective Synthesis of Spirocyclic Ethers via the Intramolecular Piancatelli Rearrangement." ChemInform 44, nr 24 (23.05.2013): no. http://dx.doi.org/10.1002/chin.201324078.

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30

Cai, Yunfei, Yurong Tang, Iuliana Atodiresei i Magnus Rueping. "Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones". Angewandte Chemie International Edition 55, nr 45 (10.10.2016): 14126–30. http://dx.doi.org/10.1002/anie.201608023.

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31

Palmer, Leoni I., i Javier Read de Alaniz. "ChemInform Abstract: Lewis Acid Catalyzed Rearrangement of Furylcarbinols: The Aza- and Oxa-Piancatelli Cascade Reaction." ChemInform 45, nr 25 (5.06.2014): no. http://dx.doi.org/10.1002/chin.201425067.

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32

Veits, Gesine K., Donald R. Wenz i Javier Read de Alaniz. "Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement". Angewandte Chemie International Edition 49, nr 49 (4.11.2010): 9484–87. http://dx.doi.org/10.1002/anie.201005131.

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33

Cai, Yunfei, Yurong Tang, Iuliana Atodiresei i Magnus Rueping. "Catalytic Asymmetric Piancatelli Rearrangement: Brønsted Acid Catalyzed 4π Electrocyclization for the Synthesis of Multisubstituted Cyclopentenones". Angewandte Chemie 128, nr 45 (10.10.2016): 14332–36. http://dx.doi.org/10.1002/ange.201608023.

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34

Veits, Gesine K., Donald R. Wenz i Javier Read de Alaniz. "Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement". Angewandte Chemie 122, nr 49 (4.11.2010): 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 i Hongjun Ren. "Catalyst-Controlled Chemodivergent Modification of Indoles with 2-Furylcarbinols: Piancatelli Reaction vs Cross-Dehydrative Coupling Reaction". Journal of Organic Chemistry 82, nr 7 (9.03.2017): 3561–70. http://dx.doi.org/10.1021/acs.joc.7b00090.

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36

Gutnov, Andrey V., Vladimir T. Abaev i Oleg P. Demidov. "Betti reaction of 2-naphthol, furfural, and acetamide: an unexpected case of secondary carbo-Piancatelli rearrangement". Chemistry of Heterocyclic Compounds 55, nr 3 (marzec 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 i David Lebœuf. "Synthesis of Bridged Tetrahydrobenzo[ b ]azepines and Derivatives through an Aza‐Piancatelli Cyclization/Michael Addition Sequence". Angewandte Chemie International Edition 59, nr 3 (27.11.2019): 1134–38. http://dx.doi.org/10.1002/anie.201911761.

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38

Palmer, Leoni I., i 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, nr 31 (17.06.2011): 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 i David Lebœuf. "Synthesis of Bridged Tetrahydrobenzo[ b ]azepines and Derivatives through an Aza‐Piancatelli Cyclization/Michael Addition Sequence". Angewandte Chemie 132, nr 3 (27.11.2019): 1150–54. http://dx.doi.org/10.1002/ange.201911761.

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40

Palmer, Leoni I., i Javier Read de Alaniz. "Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement". Angewandte Chemie 123, nr 31 (17.06.2011): 7305–8. http://dx.doi.org/10.1002/ange.201102102.

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41

Gouse, Shaik, Narra Rajashekar Reddy i Sundarababu Baskaran. "A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels–Alder Reaction: Stereoselective Synthesis of Octahydro-1H-cyclopenta[cd]isoindole". Organic Letters 21, nr 10 (8.05.2019): 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 i Jason E. Hein. "Tandem Reaction Progress Analysis as a Means for Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement". ACS Catalysis 5, nr 8 (30.06.2015): 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 i Yunfei Cai. "Ln(III)/Chiral Brønsted Acid Catalyzed Asymmetric Cascade Ring Opening/Aza-Piancatelli Rearrangement of D–A Cyclopropanes". Organic Letters 22, nr 22 (10.11.2020): 9016–21. http://dx.doi.org/10.1021/acs.orglett.0c03413.

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44

González-Pérez, Adán B., Pedro Villar i 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, nr 14 (5.04.2019): 2539–51. http://dx.doi.org/10.1002/ejoc.201900103.

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45

Veits, Gesine K., Donald R. Wenz i Javier Read de Alaniz. "ChemInform Abstract: Versatile Method for the Synthesis of 4-Aminocyclopentenones: Dysprosium (III) Triflate Catalyzed Aza-Piancatelli Rearrangement." ChemInform 42, nr 15 (17.03.2011): 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 i Biaolin Yin. "ChemInform Abstract: Synthesis, Skeletal Rearrangement, and Biological Activities of Spirooxindoles: Exploration of a Stepwise C-Piancatelli Rearrangement." ChemInform 45, nr 43 (10.10.2014): no. http://dx.doi.org/10.1002/chin.201443083.

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47

Nayani, Kiranmai, Radhika Cinsani, Anwar Hussaini SD, Prathama S. Mainkar i 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, nr 37 (9.10.2017): 5671–78. http://dx.doi.org/10.1002/ejoc.201700957.

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48

Palmer, Leoni I., i Javier Read de Alaniz. "ChemInform Abstract: Direct and Highly Diastereoselective Synthesis of Azaspirocycles by a Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." ChemInform 42, nr 51 (24.11.2011): no. http://dx.doi.org/10.1002/chin.201151090.

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49

Orozco-Saumell, Ana, Rafael Mariscal, Francisco Vila, Manuel López Granados i 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, nr 11 (25.10.2023): 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 i 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, nr 45 (30.09.2016): 16165–71. http://dx.doi.org/10.1002/chem.201603592.

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