BASE-CATALYZED REARRANGEMENT OF ALPHA-ACETOLACTATE "(2-HYDROXY-2-METHYL-3-OXOBUTANOATE) - NOVEL CARBOXYLATE ION MIGRATION IN A TERTIARY KETOL REARRANGEMENT

被引：23

作者：

CROUT, DHG

HEDGECOCK, CJR

机构：

[1] Department of Chemistry, University of Exeter, Exeter EX4 4QD, Stocker Road

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 08期

关键词：

D O I：

10.1039/p19790001982

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-catalysed racemisation of α-acetolactic acid (2-hydroxy-2-methyl-3-oxobutanoic acid) (1) has been shown to proceed by reversible tertiary ketol rearrangement with migration of the carboxylate ion rather than the methyl group. The intramolecular nature of the rearrangement was demonstrated by examination, using 13C n.m.r., of the rearrangement of [1,3-13C2]-2-hydroxy-2-methyl-3-oxobutanoate (18).

引用

页码：1982 / 1989

页数：8

共 16 条

[1] STEREOCHEMISTRY OF REDUCTOISOMERASE AND ALPHABETA-DIHYDROXYACID DEHYDRATASE-CATALYZED STEPS IN VALINE AND ISOLEUCINE BIOSYNTHESIS - OBSERVATION OF A NOVEL TERTIARY KETOL REARRANGEMENT [J].