New convenient access to thioesters of α-amino acids from N,N-disubstituted 2-aminoalk-2-enals

Abstract

N,N-Disubstituted 2-aminoalk-2-enals 1 react with alkyl- or arylthiols to give unexpected thioesters of α-amino acid 3 in good yields. The same type of product is formed when substrate 1b is treated with ethane-1,2-dithiol. The reaction proceeds via an intermediate 1,2-adduct which is transformed, after a 1,3-shift, into the final thioester 3.