Lewis acid-catalyzed ring-opening reactions of semicyclic N,O-acetals

被引：70

作者：

Sugiura, M ^{[1
]}

Kobayashi, S ^{[1
]}

机构：

[1] Univ Tokyo, CREST, Grad Sch Pharmaceut Sci, Japan Sci & Technol Corp,JST,Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 03期

关键词：

D O I：

10.1021/ol006990a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Ring opening reactions of semicyclic N,O-acetals with various nucleophiles such as silyl enol ethers are effectively catalyzed by a Lewis acid (TMSOTf). Reactions of 3-substituted N,O-acetals showed high diastereoselectivities. Synthetic utility of this method has been demonstrated in the stereoselective synthesis of an anti-malarial agent, isofebrifugine.

引用

页码：477 / 480

页数：4

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