Premium
Enantioselective and Regioselective Organocatalytic Conjugate Addition of Malonates to Nitroenynes
Author(s) -
Li XiaoJiao,
Peng FangZhi,
Li Xiang,
Wu WenTao,
Sun ZhongWen,
Li YingMei,
Zhang ShaoXiong,
Shao ZhiHui
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000561
Subject(s) - cinchona , enantioselective synthesis , conjugate , thiourea , regioselectivity , chemistry , alkyl , catalysis , organocatalysis , combinatorial chemistry , adduct , organic chemistry , aryl , mathematics , mathematical analysis
The first catalytic asymmetric conjugate addition of 1,3‐dicarbonyl compounds to nitroenynes catalyzed by cinchona alkaloid‐based thiourea organocatalysts has been developed. The 1,4‐addition adducts were obtained solely, in moderate to good yields (up to 93 %) with good enantioselectivities (up to 99 % ee ). This protocol affords a conceptually different entry to the precursors of pharmaceutically important chiral β‐alkynyl acid derivatives and synthetically useful chiral nitroalkynes. Notably, the protocol worked well with both aryl‐ and alkyl‐substituted alkynyl substrates.