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Catalytic Asymmetric Michael Reactions of α,β‐Unsaturated Ketones with Sulfonyl‐Containing Nucleophiles: Chiral Synthesis of ( R )‐Muscone and ( S )‐Celery Ketone
Author(s) -
Sun Xiaomin,
Yu Feng,
Ye Tingting,
Liang Xinmiao,
Ye Jinxing
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002418
Subject(s) - nucleophile , sulfonyl , ketone , chemistry , enantioselective synthesis , michael reaction , amine gas treating , catalysis , organic chemistry , salt (chemistry) , alkyl
An amine worth its salt : A highly enantioselective Michael addition reaction of α,β‐unsaturated ketones with the sulfonyl‐containing nucleophiles bis(phenylsulfonyl)methane and 1‐(phenylsulfonyl)propan‐2‐one, catalyzed by a chiral primary amine salt, has been developed and gives excellent enantioselectivities (see scheme). The methodology has successfully demonstrated its synthetic utility in the chiral synthesis of ( R )‐muscone and ( S )‐celery ketone.