A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S)-beta-carboxymethyl-beta-methyl-beta-lactones by asymmetric desymmetrization of HMGA anhydride

被引：21

作者：

Hashimoto, K

Kitaguchi, J

Mizuno, Y

Kobayashi, T

Shirahama, H

机构：

[1] KWANSEI GAKUIN UNIV, SCH SCI, UEGAHARA 662, JAPAN

[2] HOKKAIDO UNIV, FAC SCI, DEPT CHEM, SAPPORO, HOKKAIDO 060, JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期

关键词：

D O I：

10.1016/0040-4039(96)00274-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(R)- and (S)-beta-carboxymethyl-beta-methyl-beta-lactones, new reagents for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides were developed through the asymmetric desymmetrization of HMGA anhydride. The reagent was smoothly reacted with various alkoxide without racemization to afford the desirable half-esters. On the other hand, the reaction with various amine in refluxing toluene gave a racemic amide, The chiral HMGA amide was prepared using the corresponding methyl ester of the reagent.

引用

页码：2275 / 2278

页数：4

共 34 条

[1] DICROTALINE - THE STRUCTURE AND SYNTHESIS OF DICROTALIC ACID [J].