[3+2]-Cycloaddition Reaction between Chiral Oxaziridines and Nitriles: Enantioselective Synthesis of 2,3-Dihydro-1,2,4-oxadiazoles

Abstract

Enantiomerically pure 2,3-dihydro-1,2,4-oxadiazoles were synthesized by a cycloaddition reaction between chiral oxaziridines and nitriles. Assignment of absolute configurations was made by X-ray diffraction analysis, NOESY spectra, and theoretical calculations.

Key words

oxaziridines - oxadiazolines - stereoselectivity - cycloaddition - nitriles

References

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37

X-ray crystallographic data for 10: C₂₃H₁₉N₃OS, Mr =  85.47, 0.10 × 0.35 × 0.37 mm^³, pale orange, monoclinic, space group P21, a = 11.6205(12), b = 6.2907(5), c = 13.6858(15) Å, β = 96.168(10)˚, V = 994.66(17) Å^³, Z = 2, D _c  = 1.287 g cm^-³, λ(Mo-Kα) = 0.71073 Å, µ(Mo-Kα) = 0.181 mm^-¹. Bruker SMART APEX2 diffractometer, data collection below 2θ = 55˚, 4024 data collected, 3153 independent, 2804 observed [I > 2σ(I)]. The structure was solved by SIR2002^³8a, and refined on F^² by SHELX97^³8b. Final R = 0.0369, wR = 0.0944, on observed data, goodness-of-fit = 1.033; Flack parameters -0.03 (8); -0.21 < Δρ < 0.25 eÅ^-³. Crystallographic data, excluding structure factors, have been deposited with the Cambridge Crystallographic Data Centre as Supplementary Publication Number CCDC 767590. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone] or e-mail: [e-mail].