Resolution of racemic carboxylic acid derivatives by Ti-TADDOLate mediated esterification reactions - A general method for the preparation of enantiopure compounds

被引：104

作者：

Seebach, D ^{[1
]}

Jaeschke, G ^{[1
]}

Gottwald, K ^{[1
]}

Matsuda, K ^{[1
]}

Formisano, R ^{[1
]}

Chaplin, DA ^{[1
]}

Breuning, M ^{[1
]}

Bringmann, G ^{[1
]}

机构：

[1] UNIV WURZBURG,INST ORGAN CHEM,D-97074 WURZBURG,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(97)00456-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis-acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates 1 to cyclic carboxylic acid derivatives is described. The kinetic resolution of dioxolanones, azlactones and biaryl lactones by the Ti-TADDOLates affords, after recrystallization, ester products in highly enantioenriched form (er greater than or equal to 97:3). The enantiomer-differentiating ring-opening of a chiral cyclic anhydride by a Ti-TADDOLate leads highly enantioselectively to two constitutional isomers. (C) 1997 Elsevier Science Ltd.

引用

页码：7539 / 7556

页数：18

共 69 条

[1] BENOITON NL, 1983, PEPTIDES, P218
[2] ENZYMATIC-SYNTHESIS OF OPTICALLY-ACTIVE AMINO-ACIDS - EFFECT OF SOLVENT ON THE ENANTIOSELECTIVITY OF LIPASE-CATALYZED RING-OPENING OF OXAZOLIN-5-ONES
BEVINAKATTI, HS
BANERJI, AA
NEWADKAR, RV
MOKASHI, AA
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (12) : 1505 - 1508
[3] OPTICALLY-ACTIVE LACTONES FROM A BAEYER-VILLIGER-TYPE METAL-CATALYZED OXIDATION WITH MOLECULAR-OXYGEN
BOLM, C
SCHLINGLOFF, G
WEICKHARDT, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (18): : 1848 - 1849
[4] Bolm C., 1994, ANGEW CHEM, V106, P1944
[5] ACETOGENIC ISOQUINOLINE ALKALOIDS .15. ATROPDIASTEREOSELECTIVE RING-OPENING OF BRIDGED, AXIAL-PROSTEREOGENIC BIARYLS - DIRECTED SYNTHESIS OF (+)-ANCISTROCLADISINE
BRINGMANN, G
REUSCHER, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (12): : 1672 - 1673
[6] ATROPO-ENANTIOSELECTIVE BIARYL SYNTHESIS BY STEREOCONTROLLED CLEAVAGE OF CONFIGURATIVELY LABILE LACTONE-BRIDGED PRECURSORS USING CHIRAL H-NUCLEOPHILES
BRINGMANN, G
HARTUNG, T
[J]. TETRAHEDRON, 1993, 49 (36) : 7891 - 7902
[7] NOVEL CONCEPTS IN DIRECTED BIARYL SYNTHESIS .12. 1ST ATROPO-ENANTIOSELECTIVE RING-OPENING OF ACHIRAL BIARYLS CONTAINING LACTONE BRIDGES WITH CHIRAL HYDRIDE-TRANSFER REAGENTS DERIVED FROM BORANE
BRINGMANN, G
HARTUNG, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06): : 761 - 762
[8] BRINGMANN G, 1992, LIEBIGS ANN CHEM, P225
[9] BRINGMANN G, 1994, S AFR J CHEM-S-AFR T, V47, P83
[10] ACETOGENIC ISOQUINOLINE ALKALOIDS .14. ARYL-COUPLING VIA AXIALLY PROSTEREOGENIC LACTONES - 1ST TOTAL SYNTHESIS OF (+)-ANCISTROCLADISINE AND (OPTIONALLY) ITS ATROPISOMER
BRINGMANN, G
REUSCHER, H
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5249 - 5252

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