Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by a β-Sulfonamide Alcohol-Titanium Complex

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=substi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-12, Vol.42 (46), p.5747-5749
Main Authors: Xu, Zhaoqing, Wang, Rui, Xu, Jiangke, Da, Chao-shan, Yan, Wen-jin, Chen, Chao
Format: Article
Language:English
Subjects:
addition
aldehydes
alkynes
asymmetric catalysis
sulfonamides
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352572