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

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.

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

References

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

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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) ų, 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.

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