Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide: efficient synthesis of carboxylic 3-hydroxyacids and their derivatives.
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 beta-lactones. A mechanism is proposed to explain the synthesis of 3-hydroxyacids 1.
Concellón
José M
JM
Departamento de Química Organica e Inorganica, Facultad de Química, Universidad de Oviedo, Julian Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Concellón
Carmen
C