Received 13 December 2011
The title compound, C13H18Br2O3, was prepared by a bromination reaction of (1E,3Z)-methyl 5-oxocycloocta-1,3-dienecarboxylate, which was obtained by an epoxydation reaction of tert-butyl cyclooct-1,3-dienecarboxylate. The crystal structure confirms unequivocally the absolute configuration of both chiral centres to be S. In the crystal, C-HO interactions link the molecules into chains running along the c axis.
For the Michael addition of enantiomerically pure lithium amides, see: Davies et al. (2005). For their importance in pharmacology, see: Fülöp et al. (2001). For the reactivity of the cycloocta-1,5-diene in basic medium, see: Huber et al. (1969, 1970). For the preparation of analogous unsaturated cyclooctane esters, see: Garrido et al. (2008).
Data collection: APEX2 (Bruker 2006); cell refinement: SAINT (Bruker 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5753 ).
The authors are grateful to the FSE, the Spanish MICINN (EUI 2008-00173) and (CTQ 2009-11172/BQU) and the Junta de Castilla y Leon (Spain) for financial support (GR-178 and SA001A09). The authors also thank Grupo Santander for the doctoral fellowship awarded to MB.
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