Asymmetric synthesis of β2,3-amino acids by InI–Pd(0)-promoted metalation and addition of chiral 2-vinylaziridines

The reaction of optically active 3-alkyl-2-vinylaziridines with various aldehydes in the presence of InI and Pd(PPh3)4 gives rise to chiral syn,syn-2-vinyl-1,3-amino alcohols possessing three contiguous chiral centers stereoselectively. The ratio of the syn,syn-isomer to the other three isomers is significantly affected by the C3-substituents of aziridines as well as the alkyl groups of aldehydes. In addition, the obtained 1,3-aminoalcohols can be converted into biologically important β2,3-amino acid derivatives. [Copyright &y& Elsevier]