Introduction of a quaternary stereogenic center to oxindole using cholinesterase-catalyzed asymmetric hydrolysis

被引:17
作者
Nakazawa, K [1 ]
Hayashi, M [1 ]
Tanaka, M [1 ]
Aso, M [1 ]
Suemune, H [1 ]
机构
[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan
关键词
D O I
10.1016/S0957-4166(01)00138-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Prochiral diesters bearing an oxindole skeleton were efficiently prepared from oxindole. Cholinesterase-catalyzed hydrolysis of prochiral dipropionate afforded an optically active monoalcohol of 95% e.e. The obtained monoalcohol might find use as a versatile intermediate in the enantioselective synthesis of indole alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:897 / 901
页数:5
相关论文
共 25 条
[1]   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 [J].
Akai, S ;
Naka, T ;
Fujita, T ;
Takebe, Y ;
Kita, Y .
CHEMICAL COMMUNICATIONS, 2000, (16) :1461-1462
[2]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[3]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[4]  
2-V
[5]   A HIGHLY ENANTIOSELECTIVE HYDROLYSIS OF CIS-3,5-DIACETOXYCYCLOPENT-1-ENE - AN ENZYMATIC PREPARATION OF 3(R)-ACETOXY-5(S)-HYDROXYCYCLOPENT-1-ENE [J].
DEARDORFF, DR ;
MATTHEWS, AJ ;
MCMEEKIN, DS ;
CRANEY, CL .
TETRAHEDRON LETTERS, 1986, 27 (11) :1255-1256
[6]   Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues [J].
Edmondson, S ;
Danishefsky, SJ ;
Sepp-Lorenzino, L ;
Rosen, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2147-2155
[7]  
Fischer C, 2000, HELV CHIM ACTA, V83, P1175, DOI 10.1002/1522-2675(20000607)83:6<1175::AID-HLCA1175>3.0.CO
[8]  
2-D
[9]   Enantioselective synthesis of (-)-curcumanolide A using enzymatic transesterification of meso-spirodiol [J].
Fujita, T ;
Tanaka, M ;
Norimine, Y ;
Suemune, H ;
Sakai, K .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3824-3830
[10]   PREPARATION OF A NEW CHIRAL BUILDING-BLOCK FOR SYNTHESIZING BROADLY VARIED TYPES OF TERTIARY ALCOHOLS [J].
ITOH, T ;
OHARA, H ;
TAKAGI, Y ;
KANDA, N ;
UNEYAMA, K .
TETRAHEDRON LETTERS, 1993, 34 (26) :4215-4218