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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

✍ Scribed by Dieter Seebach; Georg Jaeschke; Konstanze Gottwald; Keiji Matsuda; Roberto Formisano; David A Chaplin; Matthias Breuning; Gerhard Bringmann

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 909 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00456-0

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✦ Synopsis

The Lewis-acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates ! 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.

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