STEREOELECTRONIC INFLUENCE ON THE NABH4 REDUCTION STEREOSELECTIVITY OF ALICYCLIC BETA-KETOESTERS

被引：5

作者：

BEESON, C

PHAM, N

DIX, TA

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

[2] UNIV CALIF IRVINE,DEPT BIOL CHEM,IRVINE,CA 92717

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 21期

关键词：

HYDRIDE REDUCTION; STEREOSELECTIVITY; KETOESTER; STEREOELECTRONIC; BOROHYDRIDE;

D O I：

10.1016/S0040-4039(00)79562-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of beta-hydroxyesters produced in the NaBH4 reduction of alicyclic-beta-ketoesters has been determined. An enhanced rate of reduction has been observed for those isomers in which the carboxylate is antiperiplanar to the hydride ion in the transition state.

引用

页码：2925 / 2928

页数：4

共 17 条

[1] CONFORMATIONAL ANALYSIS .16. ENERGY OF BOAT FORM OF CYCLOHEXANONE - DIRECT MEASUREMENTS OF 2-ALKYL KETONE EFFECTS [J].

ALLINGER, NL ;

BLATTER, HM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (04) :994-+

[2]

ANH NT, 1977, NOUV J CHIM, V1, P61

[3]

BALASUBR.SN, 1973, INDIAN J CHEM, V11, P449

[4]

BEESON C, UNPUB J ORG CHEM

[5]

BERNATH G, 1970, ACTA CHIM HUNG, V64, P81

[6]

CHEREST M, 1968, TETRAHEDRON LETT, P2205

[7]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[8]

CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041

[9]

GORDON AJ, 1972, CHEM COMPANION, P156

[10] A CORRELATION OF REACTION RATES [J].

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :334-338

← 1 2 →