1-Ethoxyvinyl 2-furoate, an efficient acyl donor for the lipase-catalyzed enantioselective desymmetrization of prochiral 2,2-disubstituted propane-1,3-diols and meso-1,2-diols

被引:27
作者
Akai, S [1 ]
Naka, T [1 ]
Fujita, T [1 ]
Takebe, Y [1 ]
Kita, Y [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
D O I
10.1039/b003871g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel acyl donor, 1-ethoxyvinyl 2-furoate, was found to produce the title reactions with high enantiotopic selectivity, high reactivity and stability of the products under various conditions.
引用
收藏
页码:1461 / 1462
页数:2
相关论文
共 18 条
[1]   Enzyme-catalyzed asymmetrization of 2,2-disubstituted 1,3-propanediols using 1-ethoxyvinyl esters [J].
Akai, S ;
Naka, T ;
Takebe, Y ;
Kita, Y .
TETRAHEDRON LETTERS, 1997, 38 (24) :4243-4246
[2]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[3]  
2-V
[4]   ENZYMATIC-HYDROLYSIS OF (+/-)-TRANS-1,2-DIACETOXYCYCLOALKANES - A FACILE ROUTE TO OPTICALLY-ACTIVE CYCLOALKANE-1,2-DIOLS [J].
CROUT, DHG ;
GAUDET, VSB ;
LAUMEN, K ;
SCHNEIDER, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :808-810
[5]   Kinetic resolution of racemic 2-substituted 3-cyclopenten-1-ols by lipase-catalyzed transesterifications: A rational strategy to improve enantioselectivity [J].
Ema, T ;
Maeno, S ;
Takaya, Y ;
Sakai, T ;
Utaka, M .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8610-8616
[6]  
Faber K, 1997, BIOTRANSFORMATIONS O, DOI 10.1007/978-3-319-61590-5
[7]   Asymmetric construction of benzylic quaternary carbons by lipase-mediated enantioselective transesterification of prochiral alpha,alpha-disubstituted 1,3-propanediols [J].
Fadel, A ;
Arzel, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (02) :283-291
[8]   Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues [J].
Fadel, A ;
GarciaArgote, S .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1159-1166
[9]   SYNTHESIS OF OLIGORIBONUCLEOTIDES .6. 2'-O-ACYL RIBONUCLEOSIDE DERIVATIVES AS INTERMEDIATES IN SYNTHESIS OF DINUCLEOSIDE PHOSPHATES [J].
FROMAGEOT, HP ;
REESE, CB ;
SULSTON, JE .
TETRAHEDRON, 1968, 24 (09) :3533-+
[10]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066