THE ADDITION OF ELECTROPHILES ON ESTER ENOLATES CONTAINING AN OXYGEN IN THE BETA-POSITION - A STEREOELECTRONICALLY CONTROLLED REACTION

被引：7

作者：

CARON, M ^{[1
]}

KAWAMATA, T ^{[1
]}

RUEST, L ^{[1
]}

SOUCY, P ^{[1
]}

DESLONGCHAMPS, P ^{[1
]}

机构：

[1] UNIV SHERBROOKE,FAC SCI,DEPT CHIM,SYNTHESE ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1986年 / 64卷 / 09期

关键词：

Esters - Olefins - Chemical reactions;

D O I：

10.1139/v86-293

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enolate anion derived from spiro ketal methyl esters (1, 3, and 4) reacts with various electrophiles (PhSeBr, Ch3I, O2, I2, (CH3S)2, and (PhS)2) to yield as the major product, the isomer resulting from an equatorial approach of the electrophilic reagent. This stereochemically controlled reaction is discussed in terms of stereoelectronic effects that increase the electron density of the a face of the enolate anion.

引用

页码：1781 / 1787

页数：7

共 19 条

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