NEW MEMBERS OF THE CHIRAL POOL - BETA-HYDROXYPIPERIDINE CARBOXYLATES FROM BAKER YEAST REDUCTIONS OF THE CORRESPONDING KETO-ESTERS

被引：44

作者：

KNIGHT, DW ^{[1
]}

LEWIS, N ^{[1
]}

SHARE, AC ^{[1
]}

HAIGH, D ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,EPSOM KT18 5XQ,SURREY,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)80164-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Baker's yeast reduction of the keto-piperidinecarboxylates 2 and 6 leads to the corresponding hydroxy-esters 3 and 7a in good chemical yields and with >99% d.e. and >93% e.e. in both cases.

引用

页码：625 / 628

页数：4

共 17 条

[1] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[2] IMPROVED METHODS FOR THE RADICAL DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

JASZBERENYI, JC .

TETRAHEDRON LETTERS, 1989, 30 (20) :2619-2622

[3]

BETTONI G, 1972, GAZZ CHIM ITAL, V102, P189

[4] A CHEMOENZYMATIC SYNTHESIS OF (+)-CASTANOSPERMINE [J].

BHIDE, R ;

MORTEZAEI, R ;

SCILIMATI, A ;

SIH, CJ .

TETRAHEDRON LETTERS, 1990, 31 (34) :4827-4830

[5] A(1,3) INTERACTION AND CONFORMATIONAL ENERGY OF AXIAL-AXIAL 1,3-DIMETHYL INTERACTION [J].

CHOW, YL ;

COLON, CJ ;

TAM, JNS .

CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (17) :2821-&

[6] EXPEDIENT SYNTHESES OF (+)-CIS-(2R,3S)-3-HYDROXYPROLINE AND (-)-(1S,5S)-2-OXA-6-AZABICYCLO[3.3.0]OCTAN-3-ONE (THE GEISSMAN-WAISS LACTONE) - FORMAL ENANTIOSELECTIVE SYNTHESES OF (-)-RETRONECINE AND RELATED PYRROLIZIDINE ALKALOIDS [J].

COOPER, J ;

GALLAGHER, PT ;

KNIGHT, DW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (08) :509-510

[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]

HOFFMANN RW, 1982, TETRAHEDRON LETT, V23, P3479

[9] HYDROXY-SUBSTITUTED AND AMINO-SUBSTITUTED PIPERIDINECARBOXYLIC ACIDS AS GAMMA-AMINOBUTYRIC ACID AGONISTS AND UPTAKE INHIBITORS [J].

JACOBSEN, P ;

LABOUTA, IM ;

SCHAUMBURG, K ;

FALCH, E ;

KROGSGAARDLARSEN, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1982, 25 (10) :1157-1162

[10]

MOTER MP, 1985, J ORG CHEM, V50, P5223

← 1 2 →