STEREOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL DISUBSTITUTED AND TRISUBSTITUTED CYCLOPENTANE DERIVATIVES USING A NEW PALLADIUM-CATALYZED CYCLIZATION

被引：31

作者：

STADTMULLER, H ^{[1
]}

TUCKER, CE ^{[1
]}

VAUPEL, A ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] PHILIPPS UNIV MARBURG,FACHBEREICH CHEM,D-35043 MARBURG,GERMANY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(00)61508-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various functionalized 5-hexenyl iodides undergo a radical ring closure to give cyclopentylmethylzinc iodides when treated with Et(2)Zn in the presence of PdCl2(dppf) (2 mol %). In the case of 4-substituted 5-hexenyl iodides trans-cyclopentanes are obtained (> 99 : 1) whereas 1-substituted-5-hexenyl iodides provide cis-cyclopentanes (ca 80 : 20). The presence of a substituent at both positions considerably improves the cis stereoselectivity up to 95 : 5.

引用

页码：7911 / 7914

页数：4

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