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Stereoselective Aldol Reactions Catalyzed by Acyclic Amino Acids in Aqueous Micelles
Author(s) -
Deng DongSheng,
Cai Jiwen
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790003
Subject(s) - chemistry , aldol reaction , catalysis , adduct , diastereomer , amino acid , stereoselectivity , aqueous solution , organic chemistry , micelle , organocatalysis , addition reaction , enantioselective synthesis , biochemistry
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‐to‐good 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.