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Chiral Thiophosphoramidate‐Catalyzed Asymmetric Michael Addition of Ketones to Nitro Olefins
Author(s) -
Lu Aidang,
Wu Ronghua,
Wang Youming,
Zhou Zhenghong,
Wu Guiping,
Fang Jianxin,
Tang Chuchi
Publication year - 2010
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.201000069
Subject(s) - chemistry , pyrrolidine , bifunctional , michael reaction , nitro , adduct , organocatalysis , catalysis , enantioselective synthesis , thio , organic chemistry , medicinal chemistry , alkyl
A novel type of pyrrolidine‐based chiral (thio)phosphoramidates was synthesized. Among them, compound ( S ,a R )‐ 3d was proven to be an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitro olefins. The corresponding adducts were obtained in good to excellent chemical yields with high levels of diastereo‐ and enantioselectivities (up to >99:1 dr and 99 % ee ).