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Chiral Thiourea‐Catalyzed Asymmetric Michael Addition of β‐Oxo Phosphonate to Nitro Olefins: Convenient Synthesis of Optically Active β‐Oxo Phosphonates
Author(s) -
Hu Kuang,
Liu Tao,
Lu A. D.,
Liu Yunfeng,
Wang Youming,
Wu Guiping,
Zhou Zhenghong,
Tang Chuchi
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100029
Subject(s) - chemistry , thiourea , michael reaction , phosphonate , cinchonine , nitro , bifunctional , enantioselective synthesis , catalysis , organocatalysis , organic chemistry , optically active , cinchona alkaloids , combinatorial chemistry , alkyl
β‐Oxo phosphonates have been proven to be alternative Michael donors in Michael addition reactions to nitro olefins in the presence of cinchonine‐based bifunctional thiourea, affording a direct and atom‐economic approach to the efficient construction of synthetically and biologically valuable chiral acyclic α‐substituted β‐oxo phosphonates with high levels of enantioselectivity (up to 98 % ee ).