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

✍ Scribed by Zhaoqing Xu; Li Lin; Jiangke Xu; Wenjin Yan; Rui Wang

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
134 KB
Volume
348
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

Highly Enantioselective Addition of Phen
Highly Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by a β-Sulfonamide Alcohol–Titanium Complex
✍ Zhaoqing Xu; Rui Wang; Jiangke Xu; Chao-shan Da; Wen-jin Yan; Chao Chen 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 89 KB 👁 2 views

The enantioselective formation of C À C bonds is an area of intense research. [1,2] The asymmetric addition of alkynyl reagents to aldehydes is very useful for the synthesis of chiral secondary propargyl alcohols, which are important building blocks for many chiral organic compounds. [3] Several stu