Optical resolution of racemic alcohols via diastereoisomeric supramolecular compound formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid

被引：36

作者：

Kassai, C

Juvancz, Z

Bálint, J

Fogassy, E

Kozma, D

机构：

[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary

[2] VITUKI Plc, H-1095 Budapest, Hungary

来源：

TETRAHEDRON | 2000年 / 56卷 / 42期

基金：

匈牙利科学研究基金会;

关键词：

O; '-dibenzoyl-(2R; 3R)-tartaric acid; (2R; racemic compounds;

D O I：

10.1016/S0040-4020(00)00776-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O,O'-Dibenzoyl-(2R,3R)-tartaric acid (DBTA) forms a hydrogen bonded supramolecular compound with alcohols. The supramolecular compound formation is enantioselective for a large number of chiral alcohols, therefore DBTA can be used as resolving agent, also for compounds having no basic group. The condition of the complex formation is that the guest molecule should contain a proton donating group and a fitting aliphatic chain or cycloalkane ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8355 / 8359

页数：5

共 26 条

[1] Optically active tetrahydrofurfuryl alcohol [J].

Balfe, MP ;

Irwin, M ;

Kenyon, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1941, :312-316

[2] A CORRELATION BETWEEN THE ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALIPHATIC AND BENZYLIC SECONDARY ALCOHOLS AND THE OPTICAL ROTATIONS OF THEIR 2,4-DINITROBENZENESULFENYL DERIVATIVES [J].

CRAINE, LE ;

BICKNELL, LK ;

MAILLOUX, RC ;

MARK, JP ;

MITCHELL, SA ;

VICENTE, SR ;

JASINSKI, JP ;

WOUDENBERG, RC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1251-1258

[3]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[4]

Farina A, 1999, ANGEW CHEM INT EDIT, V38, P2433, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2433::AID-ANIE2433>3.3.CO

[5]

2-4

[6] QUANTITATIVE APPROACH TO OPTICAL RESOLUTION [J].

FOGASSY, E ;

LOPATA, A ;

FAIGL, F ;

DARVAS, F ;

ACS, M ;

TOKE, L .

TETRAHEDRON LETTERS, 1980, 21 (07) :647-650

[7]

FUKUZAWA T, 1996, TETRAHEDRON-ASYMMETR, V7, P1649

[8]

FUKUZAWA T, 1993, TETRAHEDRON-ASYMMETR, V4, P2323

[9]

HOENIG H, 1990, SYNTHESIS-STUTTGART, V12, P1137

[10]

KASSAI C, IN PRESS SYNTH COMM

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