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An Easy, Efficient, and Completely Stereoselective Synthesis of ( E )-α,β-Unsaturated Esters via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium Diiodide or Chromium Dichloride

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


Book ID
118007181
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
79 KB
Volume
70
Category
Article
ISSN
0022-3263

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Synthesis of (E)-α,β-Unsaturated Ketones
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Direct Reaction of Dibromoacetic Acid wi
✍ Concellón, José M.; Concellón, Carmen 📂 Article 📅 2006 🏛 American Chemical Society 🌐 English ⚖ 61 KB

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.