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A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions^†

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José M. Concellón,* Pablo L. Bernad, Humberto Rodríguez-Solla, and Carmen Concellón

Departamento Qumica Orgnica e Inorgnica, Universidad de Oviedo, Julin Clavera 8, 33071 Oviedo, Spain jmcg@uniovi.es

J. Org. Chem., 2007, 72 (14), pp 5421–5423

DOI: 10.1021/jo0706271

Publication Date (Web): June 6, 2007

†

This paper is dedicated with best wishes to Professor Miguel Yus on the occasion of his 60th birthday.

Author to whom correspondence should be addressed. Phone: 34-98-510-3457. Fax: 34-98-510-3446.

Abstract

A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields and with total selectivity is reported. This reaction together with the easy and efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalkenes with total E-stereoselectivity. A mechanism is proposed to explain the E-stereoselectivity of the β-elimination reaction.

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Published In Issue July 06, 2007
Received March 27, 2007

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Note

A Convenient Samarium-Promoted Synthesis of Aliphatic (E)-Nitroalkenes under Mild Conditions^†