Catalytic enantioselective synthesis of key intermediates for triazole antifungal agents

被引:50
作者
Suzuki, M [1 ]
Kato, N [1 ]
Kanai, M [1 ]
Shibasaki, M [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Tokyo 1130033, Japan
关键词
D O I
10.1021/ol050398+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short-step synthesis of versatile chiral building blocks for triazole antifungal agents such as ZD0870 and Sch45450 was developed via catalytic enantioselective cyanosilylation of electron-deficient ketones as the key step. High enantioselectivity was produced using a catalyst prepared from Gd(HMDS)(3) and ligand 5 in a 2:3 ratio. This new catalyst preparation method was superior to the previous method using Gd((OPr)-Pr-i)(3) as a metal source. A rationale for the difference is proposed on the basis of structural studies of the catalyst complexes using ESI-MS.
引用
收藏
页码:2527 / 2530
页数:4
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