MICROBIAL DERACEMIZATION OF 1-ARYLETHANOL

被引：55

作者：

NAKAMURA, K

INOUE, Y

MATSUDA, T

OHNO, A

机构：

[1] Institute for Chemical Research, Kyoto University, Uji, Kyoto

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01255-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When racemic 1-arylethanol is reacted with Geotrichum candidum IFO 5767 in water, (R)-1-arylethanol is obtained in high yield with excellent ee. It has been found that (S)-1-arylethanol is converted into the antipode via oxidation to the corresponding aryl methyl ketone and successive reduction of the ketone to the (R)-alcohol. Allyl alcohol as an additive enhances deracemization.

引用

收藏

页码：6263 / 6266

页数：4

相关论文

共 10 条

[1]

Buisson D., 1992, Biocatalysis, V5, P249, DOI 10.3109/10242429209014871

[2] PREPARATION OF OPTICALLY-ACTIVE CYCLOHEXANEDIOLS AND (+)-ALPHA-HYDROXYCYCLOHEPTANONE BY AN ENZYME-CATALYZED STEREOINVERSION/OXIDATION PROCESS [J].

CARNELL, AJ ;

IACAZIO, G ;

ROBERTS, SM ;

WILLETTS, AJ .

TETRAHEDRON LETTERS, 1994, 35 (02) :331-334

[3] HIGH-YIELD PRODUCTION OF OPTICALLY-ACTIVE 1,2-DIOLS FROM THE CORRESPONDING RACEMATES BY MICROBIAL STEREOINVERSION [J].

HASEGAWA, J ;

OGURA, M ;

TSUDA, S ;

MAEMOTO, S ;

KUTSUKI, H ;

OHASHI, T .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (07) :1819-1827

[4] ON THE RELATION BETWEEN ELUTION ORDER AND ABSOLUTE STEREOCHEMISTRY OF ALKYLARYLCARBINOLS FROM A PIRKLE COLUMN [J].

KASAI, M ;

FROUSSIOS, C ;

ZIFFER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (04) :459-464

[5] ENANTIOSELECTIVE MICROBIAL OXIDATION OF 1-ARYLETHANOL IN AN ORGANIC-SOLVENT [J].

NAKAMURA, K ;

INOUE, Y ;

OHNO, A .

TETRAHEDRON LETTERS, 1994, 35 (25) :4375-4376

[6] STEREOCHEMICAL CONTROL OF MICROBIAL REDUCTION .17. A METHOD FOR CONTROLLING THE ENANTIOSELECTIVITY OF REDUCTIONS WITH BAKERS-YEAST [J].

NAKAMURA, K ;

KAWAI, Y ;

NAKAJIMA, N ;

OHNO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4778-4783

[7] 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

[8] ONE-STEP MICROBIAL CONVERSION OF A RACEMIC-MIXTURE OF PANTOYL LACTONE TO OPTICALLY-ACTIVE D-(-)-PANTOYL LACTONE [J].

SHIMIZU, S ;

HATTORI, S ;

HATA, H ;

YAMADA, H .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1987, 53 (03) :519-522

[9] DERACEMIZATION OF CYCLIC ALLYL ESTERS [J].

TROST, BM ;

ORGAN, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10320-10321

[10] DERACEMIZATION OF A PHOSPHINE OXIDE VIA ENANTIOSELECTIVE PROTONATION [J].

VEDEJS, E ;

GARCIARIVAS, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6517-6518