Article
Aldol-type Reactions of Unmasked Iodoacetic Acid with Carbonyl Compounds Promoted by Samarium Diiodide: Efficient Synthesis of Carboxylic 3-Hydroxyacids and Their Derivatives
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Abstract

An easy, direct, general, and efficient samarium diiodide-mediated preparation of 3-hydroxyacids 1 in high yield by reaction of different aldehydes or ketones with commercially available iodoacetic acid is described. The application of different esterification procedures to the crude 3-hydroxyacids so obtained afforded the corresponding 3-hydroxyesters. Also, the cyclization of crude 3-hydroxycarboxylic acids allowed the preparation of β-lactones. A mechanism is proposed to explain the synthesis of 3-hydroxyacids 1.
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History
- Published In Issue June 09, 2006
- Received January 19, 2006
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