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Asymmetric Addition of Phenylacetylene to Aldehydes Catalyzed by β‐Sulfonamide Alcohol‐Titanium Complex
Author(s) -
Xu Zhaoqing,
Lin Li,
Xu Jiangke,
Yan Wenjin,
Wang Rui
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505453
Subject(s) - phenylacetylene , chemistry , sulfonamide , catalysis , yield (engineering) , alcohol , ligand (biochemistry) , titanium , organic chemistry , enantioselective synthesis , medicinal chemistry , combinatorial chemistry , biochemistry , materials science , receptor , metallurgy
A series of β‐sulfonamide alcohol ligands were synthesized from L ‐phenylalanine. Titanium complexes of these compounds were used to catalyze the asymmetric addition of phenylacetylene to a number of aldehydes. When the conditions were optimized, 20 mol % of ligand 8a catalyzed the reaction with high enantioselectivity (up to 98% ee) and good yield (up to 92%). When a small amount of MeOH was added to the reaction as a modifier, as little as 5 mol % of ligand was required to efficiently catalyze the reaction under very mild conditions, resulting in an ee of up to 99% and good yield.