Stereoselective synthesis of nonracemic 1,3-amino alcohols from chiral 2-vinylaziridines by InI–Pd(0)-promoted metalation

Treatment of optically active 3-alkyl-2-vinylaziridines 1, 8 and 9 and allylic acetates 10 and 11 with InI in the presence of Pd(PPh3)4 gives rise to chiral allylindiums bearing an amino group at the δ-position, which react with several aldehydes in highly regio- and stereoselective manner to afford the syn,syn-2-vinyl-1,3-amino alcohols 2a, 5a–7a and 12a–14a possessing three contiguous chiral centers in good yields.