A chiral N-crontonyloxazolidinone Diels-Alder adduct

Abstract

(4S)-4-Benzyl-3-[(4S,5S)-(1-methoxy-5-methylcyclohexen-4-yl)carbonyl]-2-oxazolidinone, C_(19)H_(23)NO_4, M_r = 329.40, monoclinic, P2_1, a = 11.453(3), b = 7.163(4), c = 11.929(2) Å, β = 111.86(2)°, V = 908.3(5) Å^3, Z=2, D_x = 1.20 g cm^(-3), λ(Mo Kα) = 0.71073 Å, μ = 0.79 cm^(-1), F(000) = 352, T = 297 K, R = 0.034 for 885 reflections with F_o^2 > 0. The molecule is extended in the crystal; there is a small twist, -13.1 (2)°, about theamide-like C-N bond joining the oxazolidinone ring to the carbonyl group. The configurations at the two optical centers in the cyclohexene ring confirm the anticipated stereospecificity of the Diels-Alder cycloaddition synthesis.

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