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

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

*Departamento Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, P. L. Bernad, H. Rodríguez-Solla, C. Concellón, J. Org. Chem., 2007, 72, 5451-5423.

DOI: 10.1021/jo0706271 (free Supporting Information)


Abstract

A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields together with an 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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proposed mechanism



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

J. M. Concellon, H. Rodriguez-Solla, C. Simal, M. Huerta, Org. Lett., 2005, 7, 5833-5835.


Key Words

Henry Reaction, β-Elimination, Samarium Diiodide


ID: J42-Y2007-2230