A Chiral N-Crotonyloxazolidinone Diels-Alder Adduct
Marsh, Richard E.
Schaefer, William P.
Kukkola, Paivi J.
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CitationMarsh, Richard E., William P. Schaefer, Paivi J. Kukkola and Andrew G. Myers. 1992. A chiral n-crotonyloxazolidinone diels-alder adduct. Acta Crystallographica Section C: Crystal Structure Communications C48(9): 1622-1624.
Abstract(4S)-4-Benzyl-3-[(4S,5S)-(1-methoxy-5-methylcyclohexen-4-yl) carbonyl]-2-oxazolidinone, C19H23NO4, M,=329.40, monoclinic, P21, a=11.453(3), b=7.163(4), c=11.929(2)A, beta=111.86(2)o, V=908.3(5)A3, Z=2, Dx=1.20 g cm -3, wavelength(Mo Ka)=0.71073/~, u=0.79 cm-1, F(000)=352, T=297K, R=0.034 for 885 reflections with F02 greater than 0. The molecule is extended in the crystal; there is a small twist, -13.1 (2)o, about the amide-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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