Umpolung of Chiral 2-Ethynylaziridines: Indium(I)-Mediated Stereoselective Synthesis of Nonracemic 1,3-Amino Alcohols Bearing Three Chiral Centers, Catalyzed by Palladium(0)

Treatment of 3-alkyl-2-ethynylaziridines with InI in the presence of Pd(PPh(3))(4) and H(2)O gave allenylindium reagents bearing a protected amino group in high yields. Stereoselective addition of the allenylindium to aldehydes affords 2-ethynyl-1,3-amino alcohols bearing three chiral centers in good yields.