A study of asymmetric hydrocyanation of heteroaryl carboxaldehydes catalyzed by (R)-oxynitrilase under micro-aqueous conditions

被引:24
作者
Chen, PR [1 ]
Han, SQ [1 ]
Lin, GQ [1 ]
Huang, H [1 ]
Li, ZY [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(02)00005-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A number of new optically active heteroaryl cyanohydrins have been prepared by hydrocyanation under micro-aqueous conditions catalyzed by almond meal (containing (R)-oxynitrilase). Substituent effects on the reaction are discussed. This micro-aqueous method provides an efficient, convenient and economical approach to optically active cyanohydrins. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:3273 / 3279
页数:7
相关论文
共 23 条
[1]   INDOLE PHENOL BIOISOSTERISM - SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF A PYRROLO ANALOG OF LABETALOL [J].
ASSELIN, AA ;
HUMBER, LG ;
CROSILLA, D ;
OSHIRO, G ;
WOJDAN, A ;
GRIMES, D ;
HEASLIP, RJ ;
RIMELE, TJ ;
SHAW, CC .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :1009-1015
[2]   SYNTHESIS OF OPTICALLY-ACTIVE SILYL PROTECTED CYANOHYDRINS [J].
BRUSSEE, J ;
LOOS, WT ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON, 1990, 46 (03) :979-986
[3]  
EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551
[4]  
Effenberger F, 1996, ENANTIOMER, V1, P359
[5]   ENZYME-CATALYZED CYANOHYDRIN SYNTHESIS IN ORGANIC-SOLVENTS [J].
EFFENBERGER, F ;
ZIEGLER, T ;
FORSTER, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (05) :458-460
[6]   Enzyme catalyzed reactions .27. Stereoselective synthesis of thienyl and furyl analogues of ephedrine [J].
Effenberger, F ;
Eichhorn, J .
TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :469-476
[7]  
EFFENBERGER F, 2001, CURR OPIN BIOTECH, P532
[8]   Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].
Gregory, RJH .
CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682
[9]  
Gröger H, 2001, ADV SYNTH CATAL, V343, P547, DOI 10.1002/1615-4169(200108)343:6/7<547::AID-ADSC547>3.0.CO
[10]  
2-A