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Enantioselective Direct Aldol Reactions Catalyzed by Cinchonine‐derived Prolinamides
Author(s) -
ZHAO Jing,
CHEN Aijun,
LIU Quanzhong
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200990158
Subject(s) - cinchonine , chemistry , aldol reaction , enantioselective synthesis , yield (engineering) , catalysis , organic chemistry , materials science , metallurgy
Highly enantioselective aldol reactions catalyzed by cinchonine‐derived prolinamides are reported. Both cyclic and acyclic ketones were reacted with various aldehydes furnishing the desired aldol products in up to 90% yield with excellent enantioselectivities (up to 95%) and moderate diastereoselectivities (up to 3.6/1) in the case of cyclic ketones. A possible mechanism that elucidates the excellent observed enantioselectivities is presented.