RESOLUTION OF RACEMIC CARBOXYLIC-ACID DERIVATIVES BY TI-TADDOLATE MEDIATED ESTERIFICATION REACTIONS - A GENERAL-METHOD FOR THE PREPARATION OF ENANTIOPURE COMPOUNDS

Authors
SEEBACH D JAESCHKE G GOTTWALD K MATSUDA K FORMISANO R CHAPLIN DA BREUNING M BRINGMANN G
Citation
D. Seebach et al., RESOLUTION OF RACEMIC CARBOXYLIC-ACID DERIVATIVES BY TI-TADDOLATE MEDIATED ESTERIFICATION REACTIONS - A GENERAL-METHOD FOR THE PREPARATION OF ENANTIOPURE COMPOUNDS, Tetrahedron, 53(22), 1997, pp. 7539-7556
Citations number
69
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
22
Year of publication
1997
Pages
7539 - 7556
Database
ISI
SICI code
0040-4020(1997)53:22<7539:RORCDB>2.0.ZU;2-1
Abstract
The Lewis-acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates 1 to cyclic carboxylic acid derivative s 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 eq ual 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.