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Resolution of BIPHEP on Rh with a chiral diene auxiliary

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
691
Issue
10
Identifiers
DOI: 10.1016/j.jorganchem.2005.09.050
Keywords
  • Asymmetric Catalysis
  • Resolution
  • Chiral Induction

Abstract

Abstract Resolution of the atropisomeric chiral BIPHEP ligand on Rh has been achieved with the aid of 2-(4- tert-butyl-phenyl)-8-methoxy-1,8-dimethyl-bicyclo[2.2.2]octa-2,5-diene, a chiral chelating diene ligand. The diene complex 3 containing an ( S)-BIPHEP ligand was found to be configurationally stable in CDCl 3 solution at RT. Conversion of the diene complex 3 to a dicarbonyl Rh complex 4 that had a barrier of 25.0 kcal/mol for atropisomerization of the BIPHEP ligand. Preliminary studies of the use of the resolved complex 3 for catalysis are presented.

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