YEAST-MEDIATED RESOLUTION OF BETA-KETO-ESTERS OF PROCHIRAL ALCOHOLS

被引：22

作者：

HUDLICKY, T ^{[1
]}

TSUNODA, T ^{[1
]}

GADAMASETTI, KG ^{[1
]}

MURRY, JA ^{[1
]}

KECK, GE ^{[1
]}

机构：

[1] UNIV UTAH, DEPT CHEM, SALT LAKE CITY, UT 84112 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 11期

关键词：

D O I：

10.1021/jo00011a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several racemic alcohols were converted to their beta-keto esters with diketene, and the resulting compounds were subjected to kinetic resolution by means of bakers' yeast. The unreacted keto esters were separated from the reduced hydroxy esters by chromatography, and the products were analyzed for levels of enantiomeric excess. Chiral shift reagents, Mosher esters, and optical rotation of the enantiomers of the alcohols were the criteria used to determine the optical integrity of the resolved alcohols after hydrolysis of the esters. Absolute stereochemistry was determined for the resolution products of all the substrates. Some rationale is advanced to account for the observed levels of enantiomeric excess and for the apparent diastereospecificity of the enzymatic resolution. The utility of this process as means of resolution of prochiral alcohols as well as an application of such resolution to the preparation of both enantiomers of a pyrrolizidine alkaloid synthon are indicated.

引用

页码：3619 / 3623

页数：5

共 26 条

[1] CHIRAL SYNTHONS FOR THE ELABORATION OF MEVINIC ACID ANALOGS [J].