Asymmetric synthesis of tetronic acids by Blaise reaction of protected optically active cyanohydrins

被引:41
作者
Duffield, JJ [1 ]
Regan, AC [1 ]
机构
[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND
关键词
D O I
10.1016/0957-4166(96)00059-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An asymmetric synthesis of tetronic acids is described, involving the Blaise reaction of Reformatsky reagents with silyl-protected optically active cyanohydrins, which were prepared by an enzyme-catalysed method. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:663 / 666
页数:4
相关论文
共 20 条
[1]   METABOLITES OF THE HIGHER FUNGI .19. SERPENONE, 3-METHOXY-4-METHYL-5-PROP-1-ENYLFURAN-2(5H)-ONE, A NEW GAMMA-BUTYROLACTONE FROM THE FUNGUS HYPOXYLON-SERPENS (BARRONS STRAIN) (PERSOON EX FRIES)KICKX [J].
ANDERSON, JR ;
EDWARDS, RL ;
WHALLEY, AJS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (01) :215-221
[2]   NATURALLY OCCURRING LACTONES AND LACTAMES .2. ABSOLUTE CONFIGURATION OF GAMMA-METHYLTETRONIC ACID CAROLINIC ACID AND CAROLIC ACID [J].
BOLL, PM ;
SORENSEN, E ;
BALIEU, E .
ACTA CHEMICA SCANDINAVICA, 1968, 22 (10) :3251-&
[3]   STUDIES ON THE INTRAMOLECULAR CLAISEN CONDENSATION - FACILE SYNTHESIS OF TETRONIC ACIDS [J].
BRANDANGE, S ;
FLODMAN, L ;
NORBERG, A .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :927-928
[4]   SYNTHESIS OF OPTICALLY-ACTIVE ETHANOLAMINES [J].
BRUSSEE, J ;
DOFFERHOFF, F ;
KRUSE, CG ;
VANDERGEN, A .
TETRAHEDRON, 1990, 46 (05) :1653-1658
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   STUDIES WITH AMINO-ACIDS .1. SYNTHESIS OF VALINE [J].
DAVIS, JW .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) :3980-3982
[7]   NEW APPROACH TO CHIRAL 5,5-DISUBSTITUTED TETRONIC ACIDS - ENANTIOSELECTIVE SYNTHESIS OF (-)-VERTINOLIDE [J].
DESMAELE, D .
TETRAHEDRON, 1992, 48 (14) :2925-2934
[8]  
EFFENBERGER F, 1994, ANGEW CHEM INT EDIT, V33, P1555, DOI 10.1002/anie.199415551
[9]   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
[10]   IMPROVED PROCEDURE FOR THE BLAISE REACTION - A SHORT, PRACTICAL ROUTE TO THE KEY INTERMEDIATES OF THE SAXITOXIN SYNTHESIS [J].
HANNICK, SM ;
KISHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) :3833-3835