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

被引:50
作者
Ohno, H [1 ]
Hamaguchi, H [1 ]
Tanaka, T [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ol006089v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Treatment of 3-alkyl-2-ethynylaziridines with Inl in the presence of Pd(PPh3)(4) and H2O 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.
引用
收藏
页码:2161 / 2163
页数:3
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