Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4-Disubstituted Azetidines†
作者： Jean-Baptiste Denis , Géraldine Masson , Pascal Retailleau , Jieping Zhu
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摘要: Mix and go. The quinidine-amide (1)-catalyzed [2+2] cycloaddition between N-sulfonylimines (2) alkyl 2,3-butadienoate (3) afforded the (R)-azetidines 4 in excellent yields enantioselectivities. (S)-enantiomer was obtained when a quinine-amide catalyst, pseudoenantiomer of (1) used.
sci-hub.se 参考文章(119)
Marta Poch, Xavier Verdaguer, Albert Moyano, Miquel A. Pericàs, Antoni Riera, A versatile enantiospecific approach to 3-azetidinols and aziridines Tetrahedron Letters. ,vol. 32, pp. 6935- 6938 ,(1991) , 10.1016/0040-4039(91)80448-F
Francois Couty, Gwilherm Evano, Monica Vargas-Sanchez, Gloria Bouzas, Practical asymmetric preparation of azetidine-2-carboxylic acid. Journal of Organic Chemistry. ,vol. 70, pp. 9028- 9031 ,(2005) , 10.1021/JO0515881
Rafael Pedrosa, Celia Andrés, Javier Nieto, Soledad del Pozo, Diastereoselective Yang Photocyclization Reactions in Solution. Synthesis of Enantiopure Azetidin-3-ol Derivatives Journal of Organic Chemistry. ,vol. 70, pp. 1408- 1416 ,(2005) , 10.1021/JO0481497
Nacim Abermil, Géraldine Masson, Jieping Zhu, Enantioselective Aza-Morita-Baylis-Hillman Reaction Using Aliphatic α-Amidosulfones as Imine Surrogates Advanced Synthesis & Catalysis. ,vol. 352, pp. 656- 660 ,(2010) , 10.1002/ADSC.200900900
Farouk Ameer, Siegfried E. Drewes, Susan Freese, Perry T. Kaye, Rate Enhancement Effects in the Dabco Catalysed Synthesis of Hydroxyalkenoate Esters Synthetic Communications. ,vol. 18, pp. 495- 500 ,(1988) , 10.1080/00397918808060742
B. A. Bhanu Prasad, Alakesh Bisai, Vinod K. Singh, 2-aryl-N-tosylazetidines as formal 1,4-dipoles for [4 + 2] cycloaddition reactions with nitriles: an easy access to the tetrahydropyrimidine derivatives. Organic Letters. ,vol. 6, pp. 4829- 4831 ,(2004) , 10.1021/OL048161L
Valérie Declerck, Jean Martinez, Frédéric Lamaty, aza-Baylis−Hillman Reaction Chemical Reviews. ,vol. 109, pp. 1- 48 ,(2009) , 10.1021/CR068057C
Manas K. Ghorai, Amit Kumar, Deo Prakash Tiwari, BF3·OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides Journal of Organic Chemistry. ,vol. 75, pp. 137- 151 ,(2010) , 10.1021/JO902244Y
Joel Slade, Joginder Bajwa, Hui Liu, David Parker, James Vivelo, Guang-Pei Chen, John Calienni, Edwin Villhauer, Kapa Prasad, Oljan Repič, Thomas J. Blacklock, A Concise Synthesis of a Novel Insulin-Like Growth Factor I Receptor (IGF-IR) Inhibitor† Organic Process Research & Development. ,vol. 11, pp. 825- 835 ,(2007) , 10.1021/OP700052U
Veejendra K. Yadav, Vardhineedi Sriramurthy, Silylmethyl-Substituted Aziridine and Azetidine as Masked 1,3- and 1,4-Dipoles for Formal [3 + 2] and [4 + 2] Cycloaddition Reactions Journal of the American Chemical Society. ,vol. 127, pp. 16366- 16367 ,(2005) , 10.1021/JA055664T