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Chiral Sulfonated Phosphines in Enantioselective Catalysis

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Aqueous Organometallic Chemistry and Catalysis

Part of the book series: NATO ASI Series ((ASHT,volume 5))

Abstract

The imines ArC(Me)=NCHPh (Ar=Ph, 2-MeO-C6H4, 3-MeO-C6H4, 4-MeO-C6H4) are hydrogenated to the corresponding amines with extremely high enantioselectivities up to 96 % under very mild conditions, using rhodium complexes associated with sulfonated (-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane (S,S)-(BDPP). These complexes are also effective as catalyst for asymmetric hydrogenolysis of sodium cis-epoxy-succinate to sodium hydroxysuccinate in aqueous-organic two-phase solvent system or in aqueous solution. A catalytic cycle involving rhodaoxetane intermediate and a heterolytic hydrogen splitting, is suggested. Catalytic hydrogenolysis of sodium salt of trans-phenylglycidic acid proceeds via a regioselective kinetic resolution to give sodium salt of α-hydroxycarboxylic acid.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Veszprém, H-8200, Veszprém, P.O.B. 158, Hungary

    J. Bakos

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  1. J. Bakos
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Editors and Affiliations

  1. Corporate Research Laboratories, Exxon Research and Engineering Company, Annandale, New Jersey, USA

    István T. Horváth

  2. Institute of Physical Chemistry, Lajos Kossuth University, Debrecen, Hungary

    Ferenc Joó

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© 1995 Springer Science+Business Media Dordrecht

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Bakos, J. (1995). Chiral Sulfonated Phosphines in Enantioselective Catalysis. In: Horváth, I.T., Joó, F. (eds) Aqueous Organometallic Chemistry and Catalysis. NATO ASI Series, vol 5. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0355-8_23

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  • DOI: https://doi.org/10.1007/978-94-011-0355-8_23

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4158-4

  • Online ISBN: 978-94-011-0355-8

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