Umpolung of chiral 2-ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0)

H Ohno; H Hamaguchi; T Tanaka

doi:10.1021/ol006089v

Umpolung of chiral 2-ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0)

Org Lett. 2000 Jul 13;2(14):2161-3. doi: 10.1021/ol006089v.

Authors

H Ohno¹, H Hamaguchi, T Tanaka

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 10891256
DOI: 10.1021/ol006089v

Abstract

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.