Stereoselective synthesis of chiral amino allenes by organocopper- mediated anti-S(N)2'-substitution reaction of chiral ethynylaziridines

Article abstract of DOI:10.1016/S0040-4020(00)00136-8

Chiral N-protected amino allenes have been synthesized from 3-alkyl-2- ethynylaziridines via organocopper-mediated reactions. Treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-2-ethynylaziridines with RCu(CN)M (M=Li or MgX) in THF at -78°C affords exclusively the expected (S,S)-amino allenes in high yields in a regio- and stereoselective manner. On the other hand, (2S,3S)-2,3,cis-3-alkyl-2-ethynylaziridines give stereoisomeric (S,R)-amino allenes in comparable high yields. (C) 2000 Elsevier Science Ltd.