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Resolution of Racemic Carboxylic Acid Derivatives by Ti-TADDOLate Mediated Esterification Reactions : A General Method for the Preparation of Enantiopure Compounds

Title data

Seebach, Dieter ; Jaeschke, Georg ; Gottwald, Konstanze ; Matsuda, Keiji ; Formisano, Roberto ; Chaplin, David A. ; Breuning, Matthias ; Bringmann, Gerhard:
Resolution of Racemic Carboxylic Acid Derivatives by Ti-TADDOLate Mediated Esterification Reactions : A General Method for the Preparation of Enantiopure Compounds.
In: Tetrahedron. Vol. 53 (1997) Issue 22 . - pp. 7539-7556.
ISSN 0040-4020
DOI: https://doi.org/10.1016/S0040-4020(97)00456-0

Abstract in another language

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 ≥ 97:3). The enantiomer-differentiating ring-opening of a chiral cyclic anhydride by a Ti-TADDOLate leads highly enantioselectively to two constitutional isomers.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 03 Jul 2017 11:28
Last Modified: 12 Jan 2022 13:46
URI: https://eref.uni-bayreuth.de/id/eprint/38229