Tetrahedron Letters, volume 34, issue 37, pages 5885-5888

The effect of polar substituents on the conformation and stereochemistry of enolate radicals

Bernd Giese ¹

W. Damm ¹

F Wetterich ¹

H G Zeitz ¹

J Rancourt ²

Y. Guindon ^{2, 3}

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Department of Chemistry, University of Basel, St Johanns‐Ring 19, CH‐4056 Basel, Switzerland |

Bio-Méga/Boehringer Ingelheim Research Inc., 2100 rue Cunard, Laval, Québec, Canada H7S 2G5. |

Department of Chemistry, Université de Montréal, Montréal, Québec, Canada H7S 2G5. |

Publication type: Journal Article

Publication date: 1993-09-01

Elsevier

Journal: Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.323

CiteScore: 3.5

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/S0040-4039(00)73805-6

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

ESR measurements and AM1 calculations show that ester substituted radicals 2 and 6 prefer conformation A as a result of allylic strain effects. But dipolar repulsion between substituents X and CO2Et In 2 and 6 has a pronounced effect on the conformation and the stereoselectivity of radicals 2 and 6.

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Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.323

CiteScore

3.5

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)

The effect of polar substituents on the conformation and stereochemistry of enolate radicals

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