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...
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Published in: | Advanced synthesis & catalysis 2006-03, Vol.348 (4-5), p.506-514 |
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Main Authors: | , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1615-4150 1615-4169 |
DOI: | 10.1002/adsc.200505453 |