STEREOCHEMISTRY OF ENE REACTIONS OF GLYOXYLATE ESTERS

被引：52

作者：

SNIDER, BB

VANSTRATEN, JW

机构：

[1] Department of Chemistry, Princeton University, New Jersey, Princeton

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 20期

关键词：

D O I：

10.1021/jo01334a025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of the thermal and catalytic ene reactions of methyl glyoxylate is examined. With cis-2-butene at 200 °C, a 54% yield of a 7.4:1 mixture of endo-exo adducts is obtained. With cyclohexene and ferric chloride catalyst, a 4.4:1 mixture of endo-exo adducts is obtained. Trisubstituted alkenes give very little selectivity. The intramolecular ene reaction of prenyl glyoxylate proceeds at 90 °C, giving a 1:1 mixture of cis-and frans-3-isopropenyl-2-hydroxybutyrolactones. © 1979, American Chemical Society. All rights reserved.

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页码：3567 / 3571

页数：5

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