Direct Amino Acid Catalyzed Asymmetric Synthesis of Polyketide Sugars

Singlet molecular oxygen has for the first time been asymmetrically incorporated into aldehydes and ketones, and the products were isolated as their corresponding diols in good yields and ee’s.

Abstract

Back to the future: In a biomimetic asymmetric synthesis of sugars (see scheme) sequential cross-aldol reactions of simple aldehydes were catalyzed by amino acids. Deoxysugars were obtained with excellent chemoselectivity and up to >99 % ee. This transformation may implicate a prebiotic catalytic pathway in which amino acids transferred their stereochemical information to carbohydrates.