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Synthesis 2009(12): 2061-2065  
DOI: 10.1055/s-0029-1216811
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

On the Resolution of Secondary Phosphine Oxides via Diastereomeric Complex Formation: The Case of tert-Butylphenylphosphine Oxide

Jarle Holta,b,1, Anna M. Majc, Ebe P. Schuddeb, K. Michał Pietrusiewicz*c, Lełsaw Sierońd, Wanda Wieczorekd, Thomas Jerphagnonb, Isabel W. C. E. Arendsa, Ulf Hanefelda, Adriaan J. Minnaard*b
a Biocatalysis and Organic Chemistry, Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands
b Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
Fax: +48(81)5242134; e-Mail: A.J.Minnaard@rug.nl;
c Department of Organic Chemistry, Maria Curie-Skodowska University, ul. Gliniana 33, 20-614 Lublin, Poland
Fax: +31(50)3634296; e-Mail: kazimierz.pietrusiewicz@poczta.umcs.lublin.pl;
d Institute for General & Ecological Chemistry, Technical University of ŁódŸ, ¯eromskiego 116, 90-924 ŁódŸ, Poland
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Publikationsverlauf

Received 17 December 2008
Publikationsdatum:
25. Mai 2009 (online)

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Abstract

The secondary phosphine oxide, t-BuPhHP=O, the most prominent chiral member of this compound class, has been resolved in high yield and with excellent ee. This resolution discloses an efficient route to enantiopure phosphorus compounds.

Key words

secondary phosphine oxide - phosphinous acid - asymmetric catalysis - resolution - chiral ligand - P-chiral compounds

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1

Present address: School of Chemistry, University of Leeds, Leeds, LS2 9JT, UK.

33

CCDC-719981 (A) and CCDC-719982 (B) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336 033; E-mail: deposit@ccdc.cam.ac.uk.