Synthesis of optically active α-methyl β-hydroperoxy esters by diastereoselective singlet oxygen ene reaction and horseradish peroxidase catalyzed kinetic resolution

被引：3

作者：

Adam, W ^{[1
]}

Saha-Möller, CR ^{[1
]}

Weichold, O ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

MONATSHEFTE FUR CHEMIE | 2000年 / 131卷 / 06期

关键词：

gamma; delta-unsaturated beta-hydroperoxy esters; horseradish peroxidase; kinetic resolution; Schenck ene reaction; singlet oxygen;

D O I：

10.1007/s007060070098

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active diastereomeric beta-hydroperoxy esters 4 have been prepared by singlet oxygen ene reaction of beta,gamma-unsaturated esters 3 and subsequent horseradish peroxidase (HRP) catalyzed kinetic resolution of the ene product. The highest enantiomeric excess (up to 95%) has been obtained for the isopropyl ester threo-4c, which establishes that the size of the remote ester functionality exercises appreciable control in the enantioselectivity of the enzymatic kinetic resolution.

引用

页码：697 / 705

页数：9

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