PREPARATION OF HIGHLY ENANTIOPURE PYRIDYLETHANOLS BY BAKERS-YEAST REDUCTIONS

被引：15
作者：
BAILEY, D
OHAGAN, D
DYER, U
LAMONT, RB
机构：
[1] UNIV DURHAM,DEPT CHEM,SCI LABS,S RD,DURHAM DH1 3LE,ENGLAND
[2] GLAXO GRP RES LTD,WARE SG12 ODP,HERTS,ENGLAND
[3] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
来源：
TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 06期
关键词：
D O I：
10.1016/S0957-4166(00)80237-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Bakers' yeast is used to prepare 3a, 4a and 5a in high enantiomeric purity by addition of allyl alcohol to the reaction. The double reduction of 2,6-diacetylpyridine 2 with bakers' yeast leads to 5a with essentially complete enantiomeric purity predicted to be 99.97%ee.
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页码：1255 / 1258
页数：4
相关论文
共 9 条
[1]   PREPARATION AND ABSOLUTE STEREOCHEMISTRY OF ISOMERIC PYRIDYLETHANOLS AND THREO-DI(2-PYRIDYL)ETHANEDIOL [J].
IMUTA, M ;
ZIFFER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3530-3532
[2]   STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .8. STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION OF BETA-KETO-ESTERS [J].
NAKAMURA, K ;
KAWAI, Y ;
OKA, S ;
OHNO, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (03) :875-879
[3]   STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .5. EFFECT OF ALLYL ALCOHOL ON REDUCTION OF BETA-KETO-ESTERS BY BAKERS-YEAST [J].
NAKAMURA, K ;
INOUE, K ;
USHIO, K ;
OKA, S ;
OHNO, A .
CHEMISTRY LETTERS, 1987, (04) :679-682
[4]   ON THE APPLICATION OF HAMILTONS RATIO TEST TO THE ASSIGNMENT OF ABSOLUTE-CONFIGURATION AND AN ALTERNATIVE TEST [J].
ROGERS, D .
ACTA CRYSTALLOGRAPHICA SECTION A, 1981, 37 (SEP) :734-741
[5]   PREPARATION OF OPTICALLY PURE PYRIDYL-1-ETHANOLS [J].
SEEMAYER, R ;
SCHNEIDER, MP .
TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :827-830
[6]  
SERVI S, 1990, SYNTHESIS-STUTTGART, P1
[7]   STEREOCHEMICAL CONTROL OF YEAST REDUCTIONS .5. CHARACTERIZATION OF THE OXIDOREDUCTASES INVOLVED IN THE REDUCTION OF BETA-KETO-ESTERS [J].
SHIEH, WR ;
GOPALAN, AS ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (10) :2993-2994
[8]   NONLINEAR RELATIONSHIP BETWEEN THE ENANTIOSELECTIVITIES FOR ASYMMETRIC REACTIONS OF MONOFUNCTIONAL AND BIFUNCTIONAL SUBSTRATES - SYNTHESIS OF PRACTICALLY OPTICALLY PURE DIOLS BY THE CATALYTIC ENANTIOSELECTIVE DIETHYLATION OF TEREPHTHALALDEHYDE [J].
SOAI, K ;
HORI, H ;
KAWAHARA, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (02) :106-108
[9]   SYNTHESIS OF OPTICALLY-ACTIVE HETERO ALKYLARYL ALCOHOLS BY BAKER YEAST [J].
TAKESHITA, M ;
TERADA, K ;
AKUTSU, N ;
YOSHIDA, S ;
SATO, T .
HETEROCYCLES, 1987, 26 (12) :3051-3054
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