Rearrangement of N-tert-Butanesulfinyl α-Halo Imines with Alkoxides to N-tert-Butanesulfinyl 2-Amino Acetals as Precursors of NProtected and N-Unprotected α-Amino Carbonyl Compounds

摘要

Reaction of N-tert-butanesulfinyl α-halo iminesnwith alkoxides afforded new N-tert-butanesulfinyl 2-aminonacetals in good to excellent yield. These N-tert-butanesulfinyln2-amino acetals are convenient precursors for the TMSOTfpromotednsynthesis of the corresponding N-protected α-aminonaldehydes and ketones, as well as for the HCl-promotednsynthesis of 2-amino acetal hydrochlorides and α-aminonketone and α-amino aldehyde hydrochlorides in high yield.nVia this method, an asymmetric synthesis of (S)-cathinonenhydrochloride (er 94:6) was achieved.