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Versatile BoPhoz Ligands
MeBoPhoz is a mixed phosphino aminophosphine chiral ligand featuring a ferrocene backbone. The unique functional and structural features of this family of ligands have resulted in high activity and selectivity in both ruthenium, iridium and rhodium-catalyzed hydrogenation of unsaturated compounds. Due to the modular structure of the ligand, a family of different derivatives is available for screening, bearing aryl and alkoxy substituents at phosphorus.
MeBoPhoz has shown excellent activity in many rhodium - catalyzed asymmetric hydrogenation of C=C bonds in dehydroaminoacids and α, β unsaturated acids and esters (S/C up to 100,000).
The P-Cy-Me-BoPhoz ligand has been shown to catalyze the asymmetric reduction of α-ketoesters, which is unusual for a rhodium catalyst.
References:
Synthesis of an αvβ3 integrin antagonist intermediate via asymmetric hydrogenation of an α,β-unsaturated ester with BoPhoz-iridium and BoPhoz-rhodium catalysts Zanotti-Gerosa et al. Tetrahedron: Asymmetry, 2008, 19, 938-944
Phosphinoferrocenylaminophosphines as Novel and Practical Ligands for Asymmetric Catalysis
N.W. Boaz, S.D. Debenham, E. Mackenzie, S.E. Large Org. Lett., 2002, 4, 2421
Synthesis and Application of Phosphinoferrocenylaminophosphine Ligands for Asymmetric Catalysis
N.W. Boaz, S.D. Debenham, E. Mackenzie, S.E. Large, J. A. Ponasik J. Org. Chem., 2005, 70, 1872
Synthesis and Application of Phosphinoferrocenylaminophosphine Ligands for Asymmetric Catalysis N.W. Boaz, S.E. Large, J. A. Ponasik, M.K. Moore, T. Barnette, W.D. Nottingham Org.Proc.Res.Dev, 2005 9, 472
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