Facile synthesis of enantiopure 1,1′-binaphthyl-2,2′-dicarboxylic acid via lipase-catalyzed kinetic resolution

被引：40

作者：

Furutani, T ^{[1
]}

Hatsuda, M ^{[1
]}

Imashiro, R ^{[1
]}

Seki, M ^{[1
]}

机构：

[1] Tanabe Seiyaku Co Ltd, Prod & Technol Dev Lab, Yodogawa Ku, Osaka 5328505, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 24期

关键词：

D O I：

10.1016/S0957-4166(99)00555-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure 1,1'-binaphthyl-2,2'-dicarboxylic acids (R)-1 and (S)-1 have been synthesized through the lipase-catalyzed kinetic resolution of the racemic 2,2-bis(hydroxymethyl)-1,1'-binaphthyl (+/-)-2 and subsequent oxidation of the hydroxymethyl groups. (C) 2000 Elsevier Science Ltd. Air rights reserved.

引用

页码：4763 / 4768

页数：6

共 18 条

[1] CYCLISATIONS WITH HYDRAZINE .3. SYNTHESES OF PENTAPHENE AND DINAPHTHO[2,1-D-1,2'-F][1,2]DIAZOCINE [J].

BACON, RGR ;

BANKHEAD, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1963, (FEB) :839-&

[2] Efficient kinetic resolution of a racemic 7-membered biaryl lactone: enantioselective synthesis of 2,2′-dihydroxymethyl-1,1′-binaphthyl [J].

Bringmann, G ;

Hinrichs, J .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :4121-4126

[3] ACYLOXYMETHYL AS AN ACTIVATING GROUP IN LIPASE-CATALYZED ENANTIOSELECTIVE HYDROLYSIS - A VERSATILE APPROACH TO CHIRAL 4-ARYL-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATES [J].

EBIIKE, H ;

TERAO, Y ;

ACHIWA, K .

TETRAHEDRON LETTERS, 1991, 32 (41) :5805-5808

[4] 9-10-DIHYDROPHENANTHRENES .3. OPTICALLY ACTIVE 9-10-DIHYDRO-3-4-5-6-DIBENZOPHENANTHRENE [J].

HALL, DM ;

TURNER, EE .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :1242-1251

[5] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .6. PRACTICAL ASYMMETRIC-SYNTHESIS OF 1,1'-BINAPHTHYLS VIA ASYMMETRIC CROSS-COUPLING WITH A CHIRAL [(ALKOXYALKYL)FERROCENYL]MONOPHOSPHINE NICKEL-CATALYST [J].

HAYASHI, T ;

HAYASHIZAKI, K ;

KIYOI, T ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8153-8156

[6] LIPASE-CATALYZED STEREOSELECTIVE ACYLATION OF [1,1'-BINAPHTHYL]-2,2'-DIOL AND DEACYLATION OF ITS ESTERS IN AN ORGANIC-SOLVENT [J].

INAGAKI, M ;

HIRATAKE, J ;

NISHIOKA, T ;

ODA, J .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (07) :1879-1884

[7] CONVENIENT OPTICAL RESOLUTION OF AXIALLY CHIRAL 1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID [J].

KANOH, S ;

HONGOH, Y ;

MOTOI, M ;

SUDA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (03) :1032-1034

[8] KINETIC RESOLUTION OF 2-FORMYL-1,1'-BINAPHTHYLS BY BAKERS-YEAST REDUCTION OF THE FORMYL FUNCTION [J].

KAWAHARA, K ;

MATSUMOTO, M ;

HASHIMOTO, H ;

MIYANO, S .

CHEMISTRY LETTERS, 1988, (07) :1163-1164

[9] RESOLUTION OF BINAPHTHOLS AND SPIROBIINDANOLS USING CHOLESTEROL ESTERASE [J].

KAZLAUSKAS, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4953-4959

[10]

MAIGROT N, 1985, SYNTHESIS-STUTTGART, P317

← 1 2 →