Synthesis 2015; 47(20): 3118-3132
DOI: 10.1055/s-0035-1560181
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© Georg Thieme Verlag Stuttgart · New York

Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part III

Andreas Jarzebski
a  Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Email: arne.luetzen@uni-bonn.de
,
Christoph Bannwarth
b  Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4, 53115 Bonn, Germany
,
Christina Tenten
a  Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Email: arne.luetzen@uni-bonn.de
,
Christian Benkhäuser
a  Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Email: arne.luetzen@uni-bonn.de
,
Gregor Schnakenburg
c  Institut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
,
Stefan Grimme
b  Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Beringstr. 4, 53115 Bonn, Germany
,
Arne Lützen*
a  Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany   Email: arne.luetzen@uni-bonn.de
› Author Affiliations
Further Information

Publication History

Received: 08 July 2015

Accepted after revision: 04 August 2015

Publication Date:
28 August 2015 (online)


Abstract

Eleven different derivatives of Tröger’s base were synthesized and successfully resolved by (recycling) HPLC on chiral stationary (S,S)-Whelk-O1 or CHIRALPAK IA phase on a (semi-) preparative scale or synthesized in enantiomerically pure form. The absolute configuration was determined by X-ray crystal structure analysis, comparison of the quantum chemically calculated circular dichroism spectra with the experimental spectra, or comparison of specific rotations with literature data.

Supporting Information

 
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