Asymmetric Addition of Phenylacetylene to Aldehydes Catalyzed by β-Sulfonamide Alcohol-Titanium Complex

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...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-03, Vol.348 (4-5), p.506-514
Main Authors: Xu, Zhaoqing, Lin, Li, Xu, Jiangke, Yan, Wenjin, Wang, Rui
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200505453