SUBSTRATE MODIFICATION AS A MEANS OF ENHANCING THE ENANTIOSELECTIVITY OF MICROBIAL REDUCTIONS OF BETA-KETO-ESTERS - AN (R)-1,3,5-TRIHYDROXYPENTANE OR (S)-1,3,5-TRIHYDROXYPENTANE SYNTHON

被引:34
作者
BROOKS, DW [1 ]
KELLOGG, RP [1 ]
COOPER, CS [1 ]
机构
[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907
关键词
D O I
10.1021/jo00378a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:192 / 196
页数:5
相关论文
共 25 条
[1]   THE ABSOLUTE-CONFIGURATION OF OUDEMANSIN TOTAL SYNTHESIS OF (-)-OUDEMANSIN [J].
AKITA, H ;
KOSHIJI, H ;
FURUICHI, A ;
HORIKOSHI, K ;
OISHI, T .
TETRAHEDRON LETTERS, 1983, 24 (19) :2009-2010
[2]   PROOF THAT THE ABSOLUTE-CONFIGURATION OF NATURAL ALPHA-LIPOIC ACID IS R BY THE SYNTHESIS OF ITS ENANTIOMER [(S)-(-)-ALPHA-LIPOIC ACID] FROM (S)-MALIC ACID [J].
BROOKES, MH ;
GOLDING, BT ;
HOWES, DA ;
HUDSON, AT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (19) :1051-1053
[3]   REMOTE SUBSTITUENT EFFECTS IN MICROBIAL REDUCTIONS OF 3-KETOGLUTARATE AND 3-KETOADIPATE ESTERS [J].
BROOKS, DW ;
DELEE, NC ;
PEEVEY, R .
TETRAHEDRON LETTERS, 1984, 25 (41) :4623-4626
[4]   CHIRAL CYCLOHEXANOID SYNTHETIC PRECURSORS VIA ASYMMETRIC MICROBIAL REDUCTION OF PROCHIRAL CYCLOHEXANEDIONES [J].
BROOKS, DW ;
MAZDIYASNI, H ;
CHAKRABARTI, S .
TETRAHEDRON LETTERS, 1984, 25 (12) :1241-1244
[5]   REQUIREMENTS FOR STEREOSPECIFICITY IN HYDROLYSIS BY ALPHA-CHYMOTRYPSIN .4. HYDROXYL SUBSTITUENT - ABSOLUTE CONFIGURATIONS [J].
COHEN, SG ;
KHEDOURI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (20) :4228-&
[6]   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-&
[7]   ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].
DEOL, BS ;
RIDLEY, DD ;
SIMPSON, GW .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) :2459-2467
[8]  
GUZIEC FS, 1980, SYNTHESIS-STUTTGART, P691
[9]   ENANTIOSPECIFIC SYNTHESES OF TRIFUNCTIONAL (R)-3-HYDROXY ESTERS BY BAKERS-YEAST REDUCTION [J].
HIRAMA, M ;
SHIMIZU, M ;
IWASHITA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (10) :599-600
[10]   ALDOL TYPE CONDENSATIONS OF BETA-KETO ESTER DIANIONS [J].
HUCKIN, SN ;
WEILER, L .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (11) :2157-2164