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Enantioselective Organocatalytic Michael Addition of Ketones to Alkylidene Malonates
Author(s) -
Syu SiangEn,
Huang ChanHui,
Chen KoWei,
Lee ChiaJui,
Das Utpal,
Jang YeongJiunn,
Lin Wenwei
Publication year - 2012
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.22055
Subject(s) - chemistry , enantioselective synthesis , pyrrolidine , michael reaction , moiety , organocatalysis , adduct , sulfone , sulfide , organic chemistry , catalysis
Organocatalysts bearing sulfide or sulfone functions ( 1a , 1b , 1c , 1d ) were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst ( S )‐2‐((naphthalen‐2‐ylthio)methyl)pyrrolidine, bearing a pyrrolidine and a sulfide moiety, showed a very high catalytic activity in the absence of additives. The reaction condition is mild, and the Michael adducts were obtained in very good enantioselectivities (up to 96%), diastereoselectivities (up to 95:5), and chemical yields (up to 95%). Chirality 24:600–605, 2012 . © 2012 Wiley Periodicals, Inc.