Direct reaction of dibromoacetic acid with aldehydes promoted by samarium diiodide: an easy, efficient, and rapid synthesis of (E)-alpha,beta-unsaturated carboxylic acids with total stereoselectivity.

J Org Chem

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

Published: February 2006

AI Article Synopsis

  • The reaction involves dibromoacetic acid reacting with various aldehydes using samarium diiodide (SmI2) to produce (E)-alpha,beta-unsaturated carboxylic acids with high stereoselectivity.
  • This process includes an elimination step that is also facilitated by samarium diiodide.
  • A proposed mechanism is provided to explain how this transformation occurs.

Article Abstract

A promoted SmI2 direct reaction of dibromoacetic acid with different aldehydes, followed by an elimination reaction also promoted by samarium diiodide, affords (E)-alpha,beta-unsaturated carboxylic acids 2 with total stereoselectivity. A mechanism to explain this transformation is proposed.

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http://dx.doi.org/10.1021/jo052236xDOI Listing

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