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Letter

Photoinduced Metalation of Nonactivated C−Cl Bonds with Samarium Diiodide: Synthesis of Alkenes with High (Z)-Selectivity through β-Elimination Reactions^†

Supporting Info

José M. Concellón,* Humberto Rodríguez-Solla, Carmen Simal, and Mónica Huerta

Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, C/Julin Clavera, 8, 33006, Oviedo, Spain

Org. Lett., 2005, 7 (26), pp 5833–5835

DOI: 10.1021/ol0523392

Publication Date (Web): November 19, 2005

†

This paper is dedicated with best wishes to Professor Dr. Víctor Riera on the ocassion of his 70th birthday.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jmcg@fq.uniovi.es

Abstract

The photoinduced metalation of nonactivated C−Cl bonds of O-acetyl chlorohydrins is promoted by samarium diiodide. As a result of this, β-elimination of O-acetyl chlorohydrins is achieved, affording the corresponding (Z)-alkenes with total or high stereoselectivity.

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History

Published In Issue December 22, 2005
Received September 27, 2005

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Letter

Photoinduced Metalation of Nonactivated C−Cl Bonds with Samarium Diiodide: Synthesis of Alkenes with High (Z)-Selectivity through β-Elimination Reactions^†