Elimination versus diastereoselective alkylation in homochiral 2-(beta-ethoxy carbonyl) acetals

被引：11

作者：

Caballero, M ^{[1
]}

GarciaValverde, M ^{[1
]}

Pedrosa, R ^{[1
]}

Vicente, M ^{[1
]}

机构：

[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 01期

关键词：

D O I：

10.1016/0957-4166(95)00438-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of the homochiral 2-(beta-ethoxycarbonyl) dioxolane derived from (-)-exo-camphanediol with methyl iodide in the presence of one equivalent of LDA lead to the alkylated product in very good chemical yield and poor diastereomeric excess. 2-(beta-Ethoxycarbonyl)-1,3-dioxanes derived from 2,4-pentanediol behave in a different way, whereas the diequatorial form is alkylated in excellent chemical yield, the equatorial-axial diastereoisomer yields a mixture of alkylation and elimination products.

引用

页码：219 / 226

页数：8

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