Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: synthesis of alkenes with high (Z)-selectivity through beta-elimination reactions

José M Concellón; Humberto Rodríguez-Solla; Carmen Simal; Mónica Huerta

doi:10.1021/ol0523392

Photoinduced metalation of nonactivated C-Cl bonds with samarium diiodide: synthesis of alkenes with high (Z)-selectivity through beta-elimination reactions

Org Lett. 2005 Dec 22;7(26):5833-5. doi: 10.1021/ol0523392.

Authors

José M Concellón¹, Humberto Rodríguez-Solla, Carmen Simal, Mónica Huerta

Affiliation

¹ Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, C/Julián Clavería, 8, 33006, Oviedo, Spain. jmcg@fq.uniovi.es

PMID: 16354078
DOI: 10.1021/ol0523392

Abstract

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