Mimicking dihydroxy acetone phosphate-utilizing aldolases through organocatalysis: A facile route to carbohydrates and aminosugars

Abstract

(Chemical Equation Presented) A practical and environmentally friendly organocatalytic strategy designed to mimic the DHAP aldolases has been developed and shown to be effective in the preparation of carbohydrates and aminosugars. (S)-Proline and (S)-2-pyrrolidine-tetrazole catalyzed the aldol reaction between dihydroxy acetone variants such as 1,3-dioxan-5-one and 2,2-dimethyl-1,3- dioxan-5-one with aldehydes to give the corresponding polyols in good yields with very high ees. © 2005 American Chemical Society.