A convenient samarium-promoted synthesis of aliphatic (E)-nitroalkenes under mild conditions.

J Org Chem

Departamento Química Orgánica e Inorgánica, Universidad de Oviedo, JuliAn Clavería 8, 33071 Oviedo, Spain.

Published: July 2007

AI Article Synopsis

  • - A new method using samarium is reported for producing (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols, achieving high yields and full selectivity.
  • - The process of making 1-bromo-1-nitroalkan-2-ols is straightforward, providing a beneficial alternative for synthesizing nitroalkenes with complete E-stereoselectivity.
  • - A proposed mechanism is discussed that explains how the reaction achieves this specific E-stereoselectivity during the beta-elimination process.

Article 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 beta-elimination reaction.

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http://dx.doi.org/10.1021/jo0706271DOI Listing

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A convenient samarium-promoted synthesis of aliphatic (E)-nitroalkenes under mild conditions.

J Org Chem

July 2007

Departamento Química Orgánica e Inorgánica, Universidad de Oviedo, JuliAn Clavería 8, 33071 Oviedo, Spain.

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  • - The process of making 1-bromo-1-nitroalkan-2-ols is straightforward, providing a beneficial alternative for synthesizing nitroalkenes with complete E-stereoselectivity.
  • - A proposed mechanism is discussed that explains how the reaction achieves this specific E-stereoselectivity during the beta-elimination process.
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