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

doi:10.1055/s-2004-837308

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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;

Abstract

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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

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References

1a Cativiela C. Diaz-de-Villegas MD. Tetrahedron: Asymmetry 1998, 9: 3517

1b Toniolo C. Crisma M. Formaggio F. Peggion C. Biopolymers 2001, 60: 396

1c Ohfune Y. Shinada T. Bull. Chem. Soc. Jpn. 2003, 76: 1115

2a Williams RM. Hendrix JA. Chem. Rev. 1992, 92: 889

2b Duthaler RO. Tetrahedron 1994, 50: 1539

2c Gröger H. Chem. Rev. 2003, 103: 2795

3a Cogan DA. Liu G. Ellman JA. Tetrahedron 1999, 55: 8883

3b Ellman JA. Owens TD. Tang TP. Acc. Chem. Res. 2002, 35: 984

3c Zhou P. Chem B.-C. Davis FA. Tetrahedron 2004, 60: 8003

4 Bloch R. Chem. Rev. 1998, 98: 1407

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

5b Avenoza A. Busto JH. Corzana F. Peregrina JM. Sucunza D. Zurbano MM. Tetrahedron: Asymmetry 2004, 15: 131

5c Avenoza A. Busto JH. Corzana F. Peregrina JM. Sucunza D. Zurbano MM. Tetrahedron: Asymmetry 2004, 15: 719

5d Avenoza A. Busto JH. Corzana F. Jiménez-Osés G. Peregrina JM. Chem. Commun. 2004, 980

6 Olma A. Pol. J. Chem. 1996, 70: 1442

7a Marco JA. Carda M. Murga J. González F. Falomir E. Tetrahedron Lett. 1997, 38: 1841

7b Carda M. Murga J. Rodríguez S. González F. Castillo E. Marco JA. Tetrahedron: Asymmetry 1998, 9: 1703

8 Liu G. Cogan DA. Owens TD. Tang TP. Ellman JA. J. Org. Chem. 1999, 64: 1278

9 Davis FA. Lee S. Zhang H. Fanelli DL. J. Org. Chem. 2000, 65: 8704

10

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

11 Tang TP. Volkman SK. Ellman JA. J. Org. Chem. 2001, 66: 8772

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 (SHELXL97^12b), 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.