De novo synthesis of Tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3

被引：268

作者：

Fukuta, Yuhei ^{[1
]}

Mita, Tsuyoshi ^{[1
]}

Fukuda, Nobuhisa ^{[1
]}

Kanai, Motomu ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 19期

关键词：

D O I：

10.1021/ja061696k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality. Copyright © 2006 American Chemical Society.

引用

页码：6312 / 6313

页数：2

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