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Journal articles on the topic 'Aza-Piancatelli'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Zheng, Wen-Hua, Wu-Bang Tang, Kou-Sen Cao, and Shan-Shui Meng. "Boronic Acid Catalysis for Aza-Piancatelli Rearrangement." Synthesis 49, no. 16 (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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2

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

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3

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

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4

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

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5

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

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6

Marin, Lucile, Soufyan Jerhaoui, Emilie Kolodziej, et al. "Sulfoxide‐Controlled Stereoselective Aza‐Piancatelli Reaction." Advanced Synthesis & Catalysis 363, no. 17 (2021): 4277–82. http://dx.doi.org/10.1002/adsc.202100848.

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7

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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8

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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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

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

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11

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

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12

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)<sub>3</sub> 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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13

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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14

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

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15

Yu, Diana, Van T. Thai, Leoni I. Palmer, et al. "Importance of Off-Cycle Species in the Acid-Catalyzed Aza-Piancatelli Rearrangement." Journal of Organic Chemistry 78, no. 24 (2013): 12784–89. http://dx.doi.org/10.1021/jo402155b.

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16

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 (2019): 2539–51. http://dx.doi.org/10.1002/ejoc.201900103.

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17

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 (2017): 1028–31. http://dx.doi.org/10.1021/acs.orglett.6b03853.

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18

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

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19

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 (2013): no. http://dx.doi.org/10.1002/chin.201348061.

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20

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 (2010): 9674–77. http://dx.doi.org/10.1002/ange.201005131.

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21

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 (2010): 9484–87. http://dx.doi.org/10.1002/anie.201005131.

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22

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 (2014): no. http://dx.doi.org/10.1002/chin.201425067.

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23

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 (2011): 7305–8. http://dx.doi.org/10.1002/ange.201102102.

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24

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 (2011): 7167–70. http://dx.doi.org/10.1002/anie.201102102.

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25

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

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26

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

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27

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 (2019): 3822–27. http://dx.doi.org/10.1021/acs.orglett.9b01267.

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28

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 (2020): 9016–21. http://dx.doi.org/10.1021/acs.orglett.0c03413.

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29

Chung, Ryan, Diana Yu, Van T. Thai, et al. "Tandem Reaction Progress Analysis as a Means for Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement." ACS Catalysis 5, no. 8 (2015): 4579–85. http://dx.doi.org/10.1021/acscatal.5b01087.

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30

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 (2011): no. http://dx.doi.org/10.1002/chin.201115064.

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31

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 (2011): no. http://dx.doi.org/10.1002/chin.201151090.

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32

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 (2017): 5671–78. http://dx.doi.org/10.1002/ejoc.201700957.

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33

Lebœuf, David, Lucile Marin, Bastien Michelet, et al. "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 (2016): 16165–71. http://dx.doi.org/10.1002/chem.201603592.

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34

Vonteddu, Nagarjuna Reddy, Pooja R. Solanke, Kiranmai Nayani, and Srivari Chandrasekhar. "Cation Triggered Domino Aza-Piancatelli Rearrangement/Friedel–Crafts Alkylation of Indole-Tethered Furfuyl Alcohols to Access Cycloocta[b]indole Core of Alkaloids." Organic Letters 22, no. 21 (2020): 8555–60. http://dx.doi.org/10.1021/acs.orglett.0c03155.

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35

Reddy, B. V. Subba, Y. Vikram Reddy, P. Subba Lakshumma, et al. "In(OTf)3-catalyzed tandem aza-Piancatelli rearrangement/Michael reaction for the synthesis of 3,4-dihydro-2H-benzo[b][1,4]thiazine and oxazine derivatives." RSC Advances 2, no. 28 (2012): 10661. http://dx.doi.org/10.1039/c2ra21591h.

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36

"Dysprosium(III) Triflate Catalyzed Aza-Piancatelli Rearrangement." Synfacts 2011, no. 10 (2011): 1099. http://dx.doi.org/10.1055/s-0030-1261056.

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37

Subba Reddy, B. V., Y. Vikram Reddy, and Kiran Kumar Singarapu. "ChemInform Abstract: Sequential Aza-Piancatelli Rearrangement/Friedel-Crafts Alkylation for the Synthesis of Pyrrolo[1,2-d]benzodiazepine Derivatives." ChemInform 47, no. 19 (2016). http://dx.doi.org/10.1002/chin.201619160.

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38

Marin, Lucile, Guillaume Force, Vincent Gandon, Emmanuelle Schulz, and David Leboeuf. "Aza-Piancatelli Cyclization as a Platform for the Preparation of Scaffolds of Natural Compounds: Application to the Total Synthesis of Bruceolline D." European Journal of Organic Chemistry, August 11, 2020. http://dx.doi.org/10.1002/ejoc.202000849.

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