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Catalytic Asymmetric Conjugate Addition of α‐Substituted Nitro Acetates to Nitro Olefins: Enantioselective Synthesis of Highly Substituted γ‐Lactams
Author(s) -
Li YingZi,
Li Fei,
Tian Ping,
Lin GuoQiang
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.201201444
Subject(s) - chemistry , nitro , enantioselective synthesis , bifunctional , conjugate , catalysis , pyrazoline , combinatorial chemistry , organic chemistry , medicinal chemistry , mathematical analysis , alkyl , mathematics
Bifunctional bis(demethyldihydroquinine)‐catalyzed asymmetric conjugate addition of α‐substituted nitro acetates to nitro olefins is described. These addition reactions proceed smoothly with a low catalyst loading (1.0 mol‐%) at 0 °C, giving excellent diastereo‐ (up to 99:1 dr ) and enantioselectivities (up to 98 % ee ). Furthermore, highly substituted and optically pure 1‐pyrazoline and γ‐lactam have been prepared to demonstrate the synthetic application of the addition products.