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Direct Reaction of Dibromoacetic Acid with Aldehydes Promoted by Samarium Diiodide: An Easy, Efficient, and Rapid Synthesis of (E)-α,β-Unsaturated Carboxylic Acids with Total Stereoselectivity†

✍ Scribed by Concellón, José M.; Concellón, Carmen

Book ID: 115542953
Publisher: American Chemical Society
Year: 2006
Tongue: English
Weight: 61 KB
Volume: 71
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo052236x

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✦ Synopsis

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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