Download PDF
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
Further Information

Publication History

Received 17 December 2008
Publication Date:
25 May 2009 (online)

    Permissions and Reprints All articles of this category

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

    References

  • 2 Enders D. Saint-Dizier A. Lannou M.-I. Lenzen A. Eur. J. Org. Chem.  2006,  29 
    Google Scholar
  • 3 Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications   Börner A. Wiley- VCH; Weinheim: 2008. 
    Google Scholar
  • 4 Methot JL. Roush WR. Adv. Synth. Catal.  2004,  346:  1035 
    CrossrefGoogle Scholar
  • This topic has been reviewed recently, see:
  • 5a Grabulosa A. Granell J. Muller G. Coord. Chem. Rev.  2007,  251:  25 
    Google Scholar
  • 5b See also: Pietrusiewicz KM. Zablocka M. Chem. Rev.  1994,  94:  1375 
    Google Scholar
  • For a recent dynamic kinetic resolution, see:
  • 5c Bergin E. O’Connor CT. Robinson SB. McCarrigle EM. O’Mahony CP. Gilheany DG. J. Am. Chem. Soc.  2007,  129:  9566 
    Google Scholar
  • The resolution of tertiary phosphine oxides with backbone chirality has been reported a number of times, see for example:
  • 6a Netscher T. Scalone M. Schmid R. Enantioselective Hydrogenation: Towards a Large Scale Total Synthesis of (R,R,R)-α-Tocopherol, In Asymmetric Catalysis on Industrial Scale   Blaser HU. Schmidt E. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 6b Vandyck K. Matthys B. Willen M. Robeyns K. Van Meervelt L. Van der Eycken J. Org. Lett.  2006,  8:  363 
    Google Scholar
  • 6c Brunner H. Muschiol M. Zabel M. Synthesis  2008,  405 
    Google Scholar
  • For recent resolutions of P-stereogenic tertiary phosphine oxides, see:
  • 6d Novak T. Schindler J. Ujj V. Czugler M. Fogassy E. Keglevich G. Tetrahedron: Asymmetry  2006,  17:  2599 
    Google Scholar
  • 6e Novak T. Ujj V. Schindler J. Czugler M. Kubinyi M. Mayer ZA. Fogassy E. Keglevich G. Tetrahedron: Asymmetry  2007,  18:  2965 
    Google Scholar
  • 7 Berlin KD. Butler GB. Chem. Rev.  1960,  60:  243 
    CrossrefGoogle Scholar
  • 8a Ackermann L. Synthesis  2006,  1557 
    Google Scholar
  • 8b Ackermann L. Born R. Spatz JH. Althammer A. Gschrei CJ. Pure Appl. Chem.  2006,  78:  209 
    Google Scholar
  • 9 Dubrovina NV. Börner A. Angew. Chem. Int. Ed.  2004,  43:  5883 
    CrossrefPubMedGoogle Scholar
  • 10 Jiang X.-b. Minnaard AJ. Hessen B. Feringa BL. Duchateau ALL. Andrien JGO. Boogers JAF. De Vries JG. Org. Lett.  2003,  5:  1503 
    CrossrefPubMedGoogle Scholar
  • 11a Jiang X.-b. Van den Berg M. Minnaard AJ. Feringa BL. De Vries JG. Tetrahedron: Asymmetry  2004,  15:  2223 
    Google Scholar
  • 11b Galland A. Dobrota C. Toffano M. Fiaud J.-C. Tetrahedron: Asymmetry  2006,  17:  2354 
    Google Scholar
  • 12 Dai W.-M. Yeung KKY. Leung WH. Haynes RK. Tetrahedron: Asymmetry  2003,  14:  2821 
    CrossrefGoogle Scholar
  • 13 Bigeault J. Giordano L. de Riggi I. Gimbert Y. Buono G. Org. Lett.  2007,  9:  3567 
    Google Scholar
  • 14a Au-Yeung T.-L. Chan K.-Y. Haynes RK. Williams ID. Yeung LL. Tetrahedron Lett.  2001,  42:  457 
    Google Scholar
  • 14b Au-Yeung T.-L. Chan K.-Y. Chan W.-K. Haynes RK. Williams ID. Yeung LL. Tetrahedron Lett.  2001,  42:  453 
    Google Scholar
  • 15 Haynes RK. Au-Yeung TL. Chan WK. Lam WL. Li ZY. Yeung LL. Chan ACS. Li P. Koen M. Mitchell CR. Vonwiller SC. Eur. J. Org. Chem.  2000,  3205 
    CrossrefGoogle Scholar
  • 16 Imamoto T. Kikuchi S. Miura T. Wada T. Org. Lett.  2001,  3:  87 ; and references cited therein
    CrossrefPubMedGoogle Scholar
  • 17 Stankevič M. Pietrusiewicz KM. J. Org. Chem.  2007,  72:  816 
    CrossrefGoogle Scholar
  • 18a Haynes HK. Freeman RN. Mitchell CR. Vonwiller SC. J. Org. Chem.  1994,  59:  2919 
    Google Scholar
  • 19a Grishkun EV. Kolodyazhnaya AO. Kolodyazhnyi OI. Russ. J. Gen. Chem.  2003,  73:  1823 
    Google Scholar
  • 19b Kolodyazhnyi O. Andrushko NV. Grishkun EV. Russ. J. Gen. Chem.  2004,  74:  515 
    Google Scholar
  • 20a Leyris A. Bigeault J. Nuel D. Giordano L. Buono G. Tetrahedron Lett.  2007,  48:  5247 
    Google Scholar
  • 20b Moraleda D. Gatineau D. Martin D. Giordano L. Buono G. Chem. Commun.  2008,  3031 
    Google Scholar
  • 21 Leyris A. Nuel D. Giordano L. Achard M. Buono G. Tetrahedron Lett.  2005,  46:  8673 
    CrossrefGoogle Scholar
  • 22 Xu Q. Zhao C.-Q. Han L.-B. J. Am. Chem. Soc.  2008,  130:  12648 
    CrossrefPubMedGoogle Scholar
  • 23 Pfaltz A, Ribourdouille Y, Feng X, Ramalingam B, Pugin B, and Spindler F. inventors; PCT Int. Appl.  WO2007135179.  ; Chem. Abstr. 2007, 148, 11345
  • 24 Drabowicz J. Lyzwa P. Omelanczuk J. Pietrusiewicz KM. Mikolajczyk M. Tetrahedron: Asymmetry  1999,  10:  2757 
    CrossrefGoogle Scholar
  • The literature was scrutinized, but no examples of the resolution of secondary phosphine oxides/phosphinous acids via diastereomeric complex formation were found. See, next to the Chemical Abstracts:
  • 25a Handbook of Optical Resolutions via Diastereomeric Salt Formation   Kozma D. CRC Press; Boca Raton, FL: 2002. 
    Google Scholar
  • 25b Wilen SH. Tables of Resolving Agents and Optical Resolutions   Eliel EL. University of Notre Dame Press; Notre Dame, IN: 1972. 
    Google Scholar
  • 25c Newman P. Optical Resolution Procedures for Chemical Compounds   Vol 1-4:  Optical Resolution Information Center; New York: 1981-1993. 
    Google Scholar
  • 25d Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions   Wiley; New York: 1981. 
    Google Scholar
  • 26 Wang R. Polavarapu PL. Drabowicz J. Mikolajczyk M. J. Org. Chem.  2000,  65:  7561 
    CrossrefPubMedGoogle Scholar
  • 27a

    Ref. 15

  • 27b Hoffmann H. Schellenbeck P. Chem. Ber.  1966,  99:  1134 
    Google Scholar
  • 28 Ten Hoeve W. Wynberg H. J. Org. Chem.  1985,  50:  4508 
    CrossrefGoogle Scholar
  • 29 Kellogg RM. Nieuwenhuijzen JW. Pouwer K. Vries TR. Broxterman QB. Grimbergen RFP. Kaptein B. La Crois RM. de Wever E. Zwaagstra K. van der Laan AC. Synthesis  2003,  1626 
    Article in Thieme ConnectGoogle Scholar
  • 30 Vries T. Wynberg H. van Echten E. Koek J. ten Hoeve W. Kellogg RM. Broxterman QB. Minnaard A. Kaptein B. van der Sluis S. Hulshof L. Kooistra J. Angew. Chem. Int. Ed.  1998,  37:  2349 
    CrossrefPubMedGoogle Scholar
  • 31 Jacques J. Collet A. Wilen SH. Enantiomers, Racemates and Resolutions   Wiley; New York: 1981.  p.299 
    Google Scholar
  • 32 Netheton MR. Fu GC. Org. Lett.  2001,  26:  4295 
    Google Scholar
  • 34 Frenz BA. SDP-Structure Determination Package   Enraf-Nonius; Delft Holland: 1984. 
    Google Scholar
  • 35 KUMA KM-4 Software   Kuma Diffraction; Wrocaw Poland: 1992. 
    Google Scholar
  • 36 Sheldrick GM. Acta Cryst.  2008,  A64:  112 
    CrossrefPubMedGoogle Scholar
  • 37 Spek AL. J. Appl. Cryst.  2003,  36:  7 
    CrossrefGoogle Scholar
  • 38 Macrae CF. Edgington PR. McCabe P. Pidcock E. Shields GP. Taylor R. Towler M. van de Streek J. J. Appl. Cryst.  2006,  39:  453 
    Google Scholar
  • 39 Etter MC. MacDonald JC. Bernstein J. Acta Crystallogr., Sect. B  1990,  46:  256 
    CrossrefGoogle Scholar
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.