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

Authors
STADTMULLER H TUCKER CE VAUPEL A KNOCHEL P
Citation
H. Stadtmuller et al., STEREOSELECTIVE SYNTHESIS OF POLYFUNCTIONAL DISUBSTITUTED AND TRISUBSTITUTED CYCLOPENTANE DERIVATIVES USING A NEW PALLADIUM-CATALYZED CYCLIZATION, Tetrahedron letters, 34(49), 1993, pp. 7911-7914
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
49
Year of publication
1993
Pages
7911 - 7914
Database
ISI
SICI code
0040-4039(1993)34:49<7911:SSOPDA>2.0.ZU;2-L
Abstract
Various functionalized 5-hexenyl iodides undergo a radical ring closur e to give cyclopentylmethylzinc iodides when treated with Et(2)Zn in t he presence of PdCl2(dppf) (2 mol %). In the case of 4-substituted 5-h exenyl iodides trans-cyclopentanes are obtained (> 99 : 1) whereas 1-s ubstituted-5-hexenyl iodides provide cis-cyclopentanes (ca 80 : 20). T he presence of a substituent at both positions considerably improves t he cis stereoselectivity up to 95 : 5.