The Journal of organic chemistry

Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide: Efficient synthesis of carboxylic 3-hydroxyacids and their …

JM Concellón, C Concellón

Index: Concellon, Jose M.; Concellon, Carmen Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4428 - 4432

Full Text: HTML

Citation Number: 17

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 ...