S. Ramasastry, Hai-le Zhang, F. Tanaka
Jan 17, 2007
Citations
3
Influential Citations
243
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
Chiral 1,2-amino alcohols and 1,2-diols are common structural motifs found in a vast array of natural and biologically active molecules. Efficient enantioselective syntheses of ketones containing syn- or anti-1,2-amino alcohols and 1,2-diols have been reported using metal-based strategies. To date, however, approaches involving organocatalysis have been limited to the syntheses of the syn-1,2-amino alcohols and anti-1,2-diols. Herein we disclose simple and efficient routes to highly enantiomerically enriched anti-1,2-amino alcohols and syn-1,2-diols through direct asymmetric Mannich, Mannich-type, and aldol reactions involving unmodified α-hydroxyketones in reactions catalyzed by primary amine-containing amino acids. These reactions exploit (Z)-enamines of α-hydroxyketones in their bond-forming transition states. This study compliments and extends our bioorganic approach to asymmetric synthesis in these two versatile synthon classes. Significantly, these reactions are practical, tolerate wet solvent, and ...