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Acta Cryst. (2012). E68, o169  [ doi:10.1107/S1600536811053840 ]

(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butanoyl}-1,3-oxazolidin-2-one

S. Börding, C. Strohmann, H. Preut and M. Hiersemann

Abstract: The title compound, C19H24ClNO5, was synthesized and subsequently employed in an Evans alkylation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (-)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an antiperiplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an antiperiplanar arrangement with a torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

Online 17 December 2011


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