KINETIC RESOLUTION OF CHIRAL ALPHA-HYDROPEROXY ESTERS BY HORSERADISH PEROXIDASE-CATALYZED ENANTIOSELECTIVE REDUCTION TO ALPHA-HYDROXY ESTERS

被引：47

作者：

ADAM, W ^{[1
]}

FELL, RT ^{[1
]}

HOCH, U ^{[1
]}

SAHAMOLLER, CR ^{[1
]}

SCHREIER, P ^{[1
]}

机构：

[1] UNIV WURZBURG,INST PHARM & FOOD CHEM,D-97074 WURZBURG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 05期

关键词：

D O I：

10.1016/0957-4166(95)00121-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The kinetic resolution of the methyl alpha-hydroperoxy esters 4 has been investigated by horseradish peroxidase (HRP)-catalyzed reduction to the corresponding optically active alpha-hydroxy esters 5 in the presence of guaiacol. The method allows for the first time the preparation of enantiomerically pure (ee > 97%) methyl (R)-2-hydroperoxybutyrate (4a). The HRP enzyme is sensitive to the steric demand of the ester alkyl side chain, as manifested by; ethyl (ee > 97%) and isopropyl (ee 79%), while the tert-butyl derivative is not accepted by the enzyme (no reduction).

引用

页码：1047 / 1050

页数：4

共 17 条

[1] CYCLIC PEROXIDE SERIES .61. SYNTHESIS OF ALPHA-HYDROPEROXY ESTERS BY SINGLET OXYGENATION OF KETENE ACETALS [J].

ADAM, W ;

DELFIERRO, J .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (06) :1159-1161

[2]

ADAM W, 1993, ANGEW CHEM INT EDIT, V32, P1737, DOI 10.1002/anie.199317371

[3] PHOTOOXYGENATION OF SILYL KETENE ACETALS - DIOXETANES AS PRECURSORS TO ALPHA-SILYLPEROXY ESTERS IN THE SILATROPIC ENE REACTION [J].

ADAM, W ;

WANG, XH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4737-4741

[4] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[5] CONCERNING THE MECHANISM OF THE REDUCTION OF HYDROPEROXIDES BY TRISUBSTITUTED PHOSPHINES AND TRISUBSTITUTED PHOSPHITES [J].

DENNEY, DB ;

GOODYEAR, WF ;

GOLDSTEIN, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (06) :1393-1395

[6]

Dunford H.B., 1991, PEROXIDASES CHEM BIO, V2

[7] CHLOROPEROXIDASE-CATALYZED ASYMMETRIC-SYNTHESIS - ENANTIOSELECTIVE REACTIONS OF CHIRAL HYDROPEROXIDES WITH SULFIDES AND BROMOHYDRATION OF GLYCALS [J].

FU, H ;

KONDO, H ;

ICHIKAWA, Y ;

LOOK, GC ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7265-7270

[8]

HANESSIAN S, 1983, TOTAL SYNTHESIS NATU, pCH2

[9]

HOFT E, IN PRESS TETRAHEDRON

[10]

HOLLAND HL, 1992, ORGANIC SYNTHESIS OX

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