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

被引：19

作者：

Concellon, Jose M. ^{[1
]}

Concellon, Carmen ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 12期

关键词：

D O I：

10.1021/jo060118j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4428 / 4432

页数：5

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