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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;
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Publication History

Received 9 November 2004
Publication Date:
22 December 2004 (online)

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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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  • 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.

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10

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