Stereoselective Synthesis ofanti-N-Protected 3-Amino-1,2-epoxides by Nucleophilic Addition toN-tert-Butanesulfinyl Imine of a Glyceraldehyde Synthon†

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Abstract

A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2-epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

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