Efficient synthesis of enantiopure 1,2-bis(hydroxymethyl)-3,3-difluorocyclopropane derivatives through lipase-catalyzed reaction

被引:28
作者
Itoh, T [1 ]
Mitsukura, K [1 ]
Furutani, M [1 ]
机构
[1] Okayama Univ, Fac Educ, Dept Chem, Okayama 7008530, Japan
关键词
D O I
10.1246/cl.1998.903
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Efficient synthesis of chiral difluorocyclopropane building block has been accomplished; prochiral diacetate of 1,2-bis(hydroxymethyl)-3, 3-difluorocyclopropane was converted to the corresponding monoacetate through Alcaligenes sp. lipase-catalyzed hydrolysis with >99% enantiomeric excess.
引用
收藏
页码:903 / 904
页数:2
相关论文
共 18 条
[1]   Studies on mercury(II)-mediated opening of bi- and tercyclopropane arrays [J].
Barrett, AGM ;
Tam, W .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4653-4664
[2]   Regioselective ring opening of vinylcyclopropanes by hydrogenation with palladium on activated carbon [J].
Barrett, AGM ;
Tam, W .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7673-7678
[3]   Fluorinated carbenes [J].
Brahms, DLS ;
Dailey, WP .
CHEMICAL REVIEWS, 1996, 96 (05) :1585-1632
[4]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[5]   CHEMISTRY OF DIFLUOROCYCLOPROPENES - APPLICATION TO SYNTHESIS OF STEROIDAL ALLENES [J].
CRABBE, P ;
CARPIO, H ;
VELARDE, E ;
FRIED, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (08) :1478-1483
[6]   Synthesis of difluorocyclopropyl carbocyclic homo-nucleosides [J].
Csuk, R ;
Eversmann, L .
TETRAHEDRON, 1998, 54 (23) :6445-6456
[7]  
EGUSA S, 1985, B CHEM SOC JPN, V59, P3175
[8]   FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].
GELB, MH ;
SVAREN, JP ;
ABELES, RH .
BIOCHEMISTRY, 1985, 24 (08) :1813-1817
[9]  
Harada N., 1983, CIRCULAR DICHROIC SP
[10]  
ITOH T, 1998, INNOVATIVE SYNTHETIC, V283, P11