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Benzoylthiourea–Pyrrolidine as Another Bifunctional Organocatalyst: Highly Enantioselective Michael Addition of Cyclohexanone to Nitroolefins
Author(s) -
Ban Shurong,
Zhu Xixia,
Zhang Zhiping,
Xie Hongyu,
Li Qingshan
Publication year - 2013
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.201300225
Subject(s) - chemistry , cyclohexanone , pyrrolidine , bifunctional , enantioselective synthesis , michael reaction , organocatalysis , organic chemistry , catalysis
Asymmetric Michael addition of cyclohexanone to nitrostyrenes in the presence of organocatalyst 1 (10 mol‐%) and 2,4‐dichlorobenzoic acid (10 mol‐%) afforded the corresponding synthetically valuable γ‐nitroketones in moderate to good yields with high diastereoselectivities (up to >99:1 dr ) and high enantioselectivities (up to >99 % ee ) under mild conditions.