Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

Abstract

tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N–N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles.

Keywords

• amino acids
• aziridination
• organocatalysis
• ring opening
• stereoselectivity