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Highly Diastereo‐ and Enantioselective Synthesis of α‐Alkyl Norstatine Derivatives: Catalytic Asymmetric Mannich Reactions of 5 H ‐Oxazol‐4‐ones
Author(s) -
Zhao Depeng,
Wang Linqing,
Yang Dongxu,
Zhang Yixin,
Wang Rui
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.201201804
Subject(s) - enantioselective synthesis , phosphoramidate , chemistry , catalysis , mannich reaction , alkyl , organic chemistry , combinatorial chemistry , stereochemistry
Going Mannich : The title reaction results in the first catalytic asymmetric synthesis of syn ‐α‐alkyl norstatine derivatives. Excellent enantioselectivities and diastereoselectivities were achieved with a series of N ‐diphenylphosphinoyl‐protected imines and 5 H ‐oxazol‐4‐ones by using the catalyst 1 /Zn. Importantly, the involvement of the diethyl phosphoramidate 2 was critical to achieve good enantioselectivities in the present Mannich reaction.