ASYMMETRIC-SYNTHESIS OF TETRAHYDROFURANS BY DIASTEREOSELECTIVE [3+2]-CYCLOADDITION OF ALLYLSILANES WITH ALPHA-KETO ESTERS BEARING AN OPTICALLY-ACTIVE CYCLITOL AS A CHIRAL AUXILIARY

被引：54

作者：

AKIYAMA, T

YASUSA, T

ISHIKAWA, K

OZAKI, S

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, 790, Bunkyo-cho

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)74417-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tin (IV) chloride mediated [3+2] cycloadditions of allylsilanes with optically active alpha-keto esters derived from L-quebrachitol afforded tetrahydrofuran derivatives via 1,2-silyl migration with high level of diastereoselectivity. Removal of the chiral auxiliary gave silyl-substituted tetrahydrofurans of excellent optical purity.

引用

页码：8401 / 8404

页数：4

共 46 条

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OZAKI, S
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[8] SYNTHESIS OF (-)-CONDURITOL F, (+)-CONDURITOL-B, CYCLOPHELLITOL FROM L-QUEBRACHITOL
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[10] THE PREPARATION OF OPTICALLY-ACTIVE DELTA-2-ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL ACRYLOYL ESTERS BEARING CYCLITOLS AS AUXILIARIES
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