Premium
Amino Acid‐Catalyzed Asymmetric Carbohydrate Formation: Organocatalytic One‐Step De Novo Synthesis of Keto and Amino Sugars
Author(s) -
Ibrahem Ismail,
Zou Weibiao,
Xu Yongmei,
Córdova Armando
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505323
Subject(s) - chemistry , aldol reaction , amino acid , dihydroxyacetone , proline , organocatalysis , catalysis , carbohydrate synthesis , dihydroxyacetone phosphate , thiazolidine , enantioselective synthesis , yield (engineering) , organic chemistry , diamino acid , carbohydrate , stereochemistry , biochemistry , phosphate , glycerol , materials science , metallurgy , gene sequence , phylogenetic tree , gene
A direct de novo synthesis of ketoses and amino sugars by amino acid‐catalyzed asymmetric aldol, Mannich and Michael reactions with dihydroxyacetone phosphate mimics as donors is presented. Proline, proline derivatives and thiazolidine‐4‐carboxylic acids catalyzed the asymmetric assembly of keto sugars and amino sugars in high yield with up to >99% ee. The organocatalytic C 3 +C n methodology presented herein is a direct entry to the de novo synthesis of orthogonally protected C 4 , C 5 , and C 6 ketoses, carbohydrate derivatives, amino and aza sugars and the total synthesis of polyoxamic acids. The addition of water significantly accelerated and improved the enantioselectivity of the proline‐mediated biomimetic asymmetric CC bond‐forming reactions.