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Organocatalytic enantioselective Michael addition of malononitrile to nitroolefins catalyzed by bifunctional thiourea
Author(s) -
Guo HaiMing,
Li JianGuo,
Qu GuiRong,
Zhang XiaoMei,
Yuan WeiCheng
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20956
Subject(s) - malononitrile , chemistry , bifunctional , thiourea , enantioselective synthesis , michael reaction , amine gas treating , organic chemistry , organocatalysis , enantiomeric excess , catalysis , enantiomer , yield (engineering) , adduct , combinatorial chemistry , materials science , metallurgy
A novel enantioselective Michael addition of malononitrile to trans‐β‐nitroolefins in the presence of bifunctional amine thiourea organocatalyst is developed. The Michael reaction catalyzed by amine thioureas containing both central and axial chiral elements proceeded smoothly and provided the desired adducts with high yields (up to 96% yield) and moderate enantioselectivities (up to 83% enantiomeric excess). Chirality, 2011. © 2011 Wiley‐Liss, Inc.