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Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide‐Based Phosphines
Author(s) -
Han Xiaoyu,
Zhong Fangrui,
Wang Youqing,
Lu Yixin
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201106672
Subject(s) - enantioselective synthesis , yield (engineering) , dipeptide , catalysis , combinatorial chemistry , aryl , chemistry , computer science , alkyl , organic chemistry , peptide , materials science , biochemistry , metallurgy
A fast one : The title reaction proceeds in the presence of 5 mol % of the catalyst 1 , and is complete within an hour. The 2‐alkyl‐ and 2‐aryl‐substituted 3‐pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of (+)‐trachelanthamidine is also demonstrated. Boc= tert ‐butoxycarbonyl, M.S.=molecular sieves, TBDPS= tert ‐butyldiphenylsilyl.