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Highly Enantio‐ and Diastereoselective Reactions of γ‐Substituted Butenolides Through Direct Vinylogous Conjugate Additions
Author(s) -
Zhang Wen,
Tan Davin,
Lee Richmond,
Tong Guanghu,
Chen Wenchao,
Qi Baojian,
Huang KuoWei,
Tan ChoonHong,
Jiang Zhiyong
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.201205872
Subject(s) - conjugate , chemistry , thiourea , amine gas treating , alkyl , aryl , catalysis , stereochemistry , medicinal chemistry , organic chemistry , mathematics , mathematical analysis
The strength of the weak : An L ‐tert‐ leucine‐derived amine–thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ‐aryl‐ and alkyl‐substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non‐bonding interactions, which stabilize the transition state.