Novel camphor-derived chiral auxiliaries:: Significant solvent and additive effects on asymmetric reduction of chiral α-keto esters

被引：40

作者：

Chu, YY ^{[1
]}

Yu, CS ^{[1
]}

Chen, CJ ^{[1
]}

Yang, KS ^{[1
]}

Lain, JC ^{[1
]}

Lin, CH ^{[1
]}

Chen, KM ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 19期

关键词：

D O I：

10.1021/jo9902188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective reduction of various alpha-keto esters 5a-d derived from exo-10,10-diphenyl-2,10-camphanediol 4a and exo-10,10-diphenyl-10-methoxy-2-camphanol 4b is described. High to excellent diastereomeric excess (99% de) with good chemical yields is obtained. The sense of stereoselectivity as a function of C10 modification is remarkable. Further, in the case of 5d, both diastereomers of a-hydroxyl esters can be obtained with excellent optical purity by the appropriate choice of reaction conditions. The influence of the solvents and additives on the reaction course has been investigated.

引用

页码：6993 / 6998

页数：6

共 27 条

[1] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].