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

Jarle Holt; Anna M. Maj; Ebe P. Schudde; K. Michał Pietrusiewicz; Lełsaw Sieroń; Wanda Wieczorek; Thomas Jerphagnon; Isabel W. C. E. Arends; Ulf Hanefeld; Adriaan J. Minnaard

doi:10.1055/s-0029-1216811

PAPER

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

Jarle Holt^a,b,1, Anna M. Maj^c, Ebe P. Schudde^b, K. Michał Pietrusiewicz*^c, Lełsaw Sieroń^d, Wanda Wieczorek^d, Thomas Jerphagnon^b, Isabel W. C. E. Arends^a, Ulf Hanefeld^a, 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

Abstract

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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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Referenzen

References

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

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