Chemistry of aminoketene dithioacetals: preparation of protected α-amino aldehydes and ketones and formation of nitrogen heterocycles

Abstract

The ambident anion (2) derived from primary aminoketene dithioacetal (1, R = Ph) reacts with alkyl halides at the carbon atom to give remarkably stable primary imines which may be reduced to give protected α-amino ketones using borane in quantitative yield, and under similar conditions aminoketene dithioacetal (1, R = Ph) gives the protected α-amino aldehyde (15); anion (2) reacts with the bis-electrophile epichlorohydrin to give the nitrogen heterocycle (9) in 80% yield, and other related chemistry is also reported.