Stereoselective Aldol Reactions Catalyzed by Acyclic Amino Acids in Aqueous Micelles

✍ Scribed by Dong-Sheng Deng; Jiwen Cai

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: German
• Weight: 75 KB
• Volume: 90
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200790003

✦ Synopsis

The catalytic properties of all proteinogenic, acyclic amino acids for direct aldol reaction in H 2 O, assisted by various surfactants, were investigated. The basic and neutral amino acids were shown to be efficient catalysts, giving rise to good-to-excellent yields of adducts (up to 95%), with moderate-togood diastereoselectivities (up to 86%), L-arginine being the most-effective catalyst. The syn/anti diastereoisomer ratio could be readily tuned by proper choice of the amino acid used. Also, the range of substrates that underwent the reaction was extended to less-reactive aldehydes carrying electron-donating Br substituents.