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Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by a β‐Sulfonamide Alcohol–Titanium Complex
Author(s) -
Xu Zhaoqing,
Wang Rui,
Xu Jiangke,
Da Chaoshan,
Yan Wenjin,
Chen Chao
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352572
Subject(s) - phenylacetylene , sulfonamide , enantioselective synthesis , propargyl alcohol , alcohol , catalysis , chemistry , titanium , organic chemistry , aldehyde
Three simple steps were required to prepare the β‐sulfonamide alcohol ligand (L*) from L ‐phenylalanine. Its titanium complex efficiently catalyzes the asymmetric addition of phenylacetylene ( 2 ) to aromatic aldehydes 1 to form enantiomerically pure propargyl alcohols 3 . Ts= p ‐toluenesulfonyl, R=substituted phenyl or naphthyl group.