Nucleophilic substitution of protected beta-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of beta-functionalized phenethyl substrates

被引：18

作者：

Hudlicky, T

Endoma, MAA

Butora, G

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 17期

关键词：

D O I：

10.1039/p19960002187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(5S,6R)-1-(2-Bromoethyl)-5,6-(propane-2,2-diyldioxy)cyclohexa-1, 3-diene 6 is subjected to nucleophilic substitution reaction using C-, N-, O- and S-based nucleophiles. The yields of the products are compared with those obtained by direct microbial oxidation of the corresponding aromatic substrates. The enantiomeric excess and isolated yield for each compound are reported.

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页码：2187 / 2192

页数：6

相关论文

共 23 条

[1] STRUCTURE AND STEREOCHEMISTRY OF CIS-DIHYDRO DIOL AND PHENOL METABOLITES OF BICYCLIC AZAARENES FROM PSEUDOMONAS-PUTIDA UV4 [J].

BOYD, DR ;

SHARMA, ND ;

DORRITY, MRJ ;

HAND, MV ;

MCMORDIE, RAS ;

MALONE, JF ;

PORTER, HP ;

DALTON, H ;

CHIMA, J ;

SHELDRAKE, GN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1065-1071

[2] CHEMOENZYMATIC SYNTHESIS OF THE 2,3-CIS-DIHYDRODIOL AND 3,4-CIS-DIHYDRODIOL ENANTIOMERS OF MONOSUBSTITUTED BENZENES [J].

BOYD, DR ;

SHARMA, ND ;

BARR, SA ;

DALTON, H ;

CHIMA, J ;

WHITED, G ;

SEEMAYER, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1147-1148

[3]

Brown S.M., 1993, ORGANIC SYNTHESIS TH, V2, P113

[4] THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS [J].

CARLESS, HAJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (07) :795-826

[5] THERMAL AND PHOTOCHEMICAL-REACTIONS OF ORGANOCOBALOXIMES WITH DIPHENYL DISULFIDE AND DIPHENYL DISELENIDE [J].

DENIAU, J ;

DUONG, KNV ;

GAUDEMER, A ;

BOUGEARD, P ;

JOHNSON, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1981, (02) :393-398

[6]

GREWE R, 1953, LIEBIGS ANN CHEM, V581, P85

[7] PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES TO THE FREE CIS-DIOL METABOLITE PRODUCED FROM THE OXIDATION OF BROMOBENZENE BY PSEUDOMONAS-PUTIDA - SYNTHESIS OF NEW HOMOCHIRAL 3-ALKYNYL CIS-CYCLOHEXA-3,5-DIENE-1,2-DIOLS [J].

HUDLICKY, T ;

BOROS, EE .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :217-220

[8]

HUDLICKY T, 1994, J BIOORG MED CHEM, V2, P727

[9]

HUDLICKY T, 1995, TETRAHEDRON-ASYMMETR, V6, P537

[10]

HUDLICKY T, 1995, ADV ASYMMETRIC SYNTH, V1, P271