Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5'-hydantoinyl)cyclohexane

被引：22

作者：

Yokomatsu, T

Nakabayashi, N

Matsumoto, K

Shibuya, S

机构：

[1] TOKYO UNIV PHARM & LIFE SCI,SCH PHARM,HACHIOJI,TOKYO 19203,JAPAN

[2] TAISHO PHARMACEUT CO LTD,RES CTR,OMIYA,SAITAMA 330,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期

关键词：

D O I：

10.1016/0957-4166(95)00403-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane 1 by lipase has been developed. The transesterification of (+/-)-1 with vinyl acetate in the presence of Lipase AK without solvent proceeded to give (+)-1 and the corresponding acetate (+)-5 in good yield and high enantiomeric ratio. The alcohol (+)-1 was transformed to the optically active hydantoins 12 and 13, possible intermediates for the synthesis of conformational constrained analogues of AP-5.

引用

页码：3055 / 3062

页数：8

共 19 条

[1]

Alder U., 1989, TETRAHEDRON LETT, V30, P1793

[2] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].