PDF herunterladen
Synthesis 2005(4): 575-578  
DOI: 10.1055/s-2004-837308
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of (S)- and (R)-α-Phenylserine by a Sulfinimine-Mediated Strecker Reaction

Alberto Avenoza*, Jesús H. Busto, Francisco Corzana, Jesús M. Peregrina*, David Sucunza, María M. Zurbano
Departamento de Química, Universidad de La Rioja, Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., 26006 Logroño, Spain
Fax: +34(941)299655; e-Mail: alberto.avenoza@dq.unirioja.es; e-Mail: jesusmanuel.peregrina@dq.unirioja.es;
Weitere Informationen

Publikationsverlauf

Received 9 November 2004
Publikationsdatum:
22. Dezember 2004 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A straightforward and efficient diastereoselective synthesis of (S)- and (R)-α-phenylserine is reported. The key step involves an asymmetric Strecker reaction of a chiral N-sulfinyl ketimine, which was obtained from the commercially available 2-hydroxyacetophenone.

Key words

amino acids - asymmetric synthesis - imines - nitriles - nucleophilic addition

    References

  • 1a Cativiela C. Diaz-de-Villegas MD. Tetrahedron: Asymmetry  1998,  9:  3517 
    CrossrefGoogle Scholar
  • 1b Toniolo C. Crisma M. Formaggio F. Peggion C. Biopolymers  2001,  60:  396 
    CrossrefGoogle Scholar
  • 1c Ohfune Y. Shinada T. Bull. Chem. Soc. Jpn.  2003,  76:  1115 
    CrossrefGoogle Scholar
  • 2a Williams RM. Hendrix JA. Chem. Rev.  1992,  92:  889 
    CrossrefGoogle Scholar
  • 2b Duthaler RO. Tetrahedron  1994,  50:  1539 
    CrossrefGoogle Scholar
  • 2c Gröger H. Chem. Rev.  2003,  103:  2795 
    CrossrefGoogle Scholar
  • 3a Cogan DA. Liu G. Ellman JA. Tetrahedron  1999,  55:  8883 
    CrossrefGoogle Scholar
  • 3b Ellman JA. Owens TD. Tang TP. Acc. Chem. Res.  2002,  35:  984 
    CrossrefGoogle Scholar
  • 3c Zhou P. Chem B.-C. Davis FA. Tetrahedron  2004,  60:  8003 
    CrossrefGoogle Scholar
  • 4 Bloch R. Chem. Rev.  1998,  98:  1407 
    CrossrefPubMedGoogle Scholar
  • 5a Avenoza A. Cativiela C. Corzana F. Peregrina JM. Sucunza D. Zurbano MM. In Targets in Heterocyclic Systems   Attanasi OA. Spinelli D. Italian Society of Chemistry; Rome: 2002.  p.231-244  ; and references cited therein
    CrossrefGoogle Scholar
  • 5b Avenoza A. Busto JH. Corzana F. Peregrina JM. Sucunza D. Zurbano MM. Tetrahedron: Asymmetry  2004,  15:  131 
    CrossrefGoogle Scholar
  • 5c Avenoza A. Busto JH. Corzana F. Peregrina JM. Sucunza D. Zurbano MM. Tetrahedron: Asymmetry  2004,  15:  719 
    CrossrefGoogle Scholar
  • 5d Avenoza A. Busto JH. Corzana F. Jiménez-Osés G. Peregrina JM. Chem. Commun.  2004,  980 
    CrossrefGoogle Scholar
  • 6 Olma A. Pol. J. Chem.  1996,  70:  1442 
    Google Scholar
  • 7a Marco JA. Carda M. Murga J. González F. Falomir E. Tetrahedron Lett.  1997,  38:  1841 
    CrossrefGoogle Scholar
  • 7b Carda M. Murga J. Rodríguez S. González F. Castillo E. Marco JA. Tetrahedron: Asymmetry  1998,  9:  1703 
    CrossrefGoogle Scholar
  • 8 Liu G. Cogan DA. Owens TD. Tang TP. Ellman JA. J. Org. Chem.  1999,  64:  1278 
    CrossrefGoogle Scholar
  • 9 Davis FA. Lee S. Zhang H. Fanelli DL. J. Org. Chem.  2000,  65:  8704 
    CrossrefPubMedGoogle Scholar
  • 11 Tang TP. Volkman SK. Ellman JA. J. Org. Chem.  2001,  66:  8772 
    CrossrefGoogle Scholar
  • 12a

    Crystal data of compound 1: C39H54N6O6S3, M w = 799.06, colorless prism of 0.30 × 0.12 × 0.10 mm, T = 173 K, orthorhombic, space group P 21 21 21, Z = 4, a = 12.5430 (10) Å, b = 18.4770 (10) Å, c = 18.5730 (10) Å, α = 90.000(10), β = 90.000(10), γ = 90.000(10)°, V = 4304.4 (5) Å3, d calc = 1.233 g cm-3, F(000) = 1704, λ = 0.71073 Å (Mo, Kα), µ = 0.086 mm-1, Nonius kappa CCD diffractometer, θ range 1.55-25.01°, 7270 collected reflections, 7241 unique, full-matrix least-squares (SHELXL9712b), R1 = 0.0586, wR2 = 0.1142, (R1 = 0.1026, wR2 = 0.1304 all data), goodness of fit = 1.029, residual electron density between 0.254 and -0.263 e Å-3. Hydrogen atoms fitted at theoretical positions. Further details on the crystal structure are available on request from Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, UK on quoting the depository number 246445.

  • 12b Sheldrick GM. SHELXL97, Program for the Refinement of Crystal Structures   University of Göttingen; Germany: 1997. 
    Google Scholar
10

HPLC conditions: Lichrospher Si (5 µm, 250 × 4.6 mm), hexane-MTBE = 70:30, 0.6 mL/min, 265 nm, 25 °C.