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Showing papers by "Matthias Breuning published in 1997"

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

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Dieter Seebach1, Georg Jaeschke1, Konstanze Gottwald1, Keiji Matsuda1, Roberto Formisano1, David A Chaplin1, Matthias Breuning2, Gerhard Bringmann2 •
ETH Zurich1, University of Würzburg2
02 Jun 1997-Tetrahedron
TL;DR: In this paper, 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.

95 citations

Journal Article•DOI•
Resolution of Racemic Carboxylic Acid Derivatives by Ti‐TADDOLate Mediated Esterification Reactions ‐ A General Method for the Preparation of Enantiopure Compounds.

[...]

Dieter Seebach1, Georg Jaeschke1, Konstanze Gottwald1, Keiji Matsuda1, Roberto Formisano1, David A Chaplin1, Matthias Breuning2, Gerhard Bringmann2 •
ETH Zurich1, University of Würzburg2
30 Sep 1997-ChemInform
TL;DR: In this paper, 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.
Abstract: 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.