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Intramolecular cycloaddition reactions of two furfuryl fumarates yield, after crystallization, pure diastereomers of oxabicyclo[2.2.1]heptene derivatives which are versatile starting points for the total synthesis of natural products. The crystal structures of the adducts, menthyl (3aS,6R,7R,7aR)-1,3,3a,6,7,7a-hexahydro-3,3-dimethyl-1-oxo-3a,6-epoxyisobenzofuran-7-carboxylate, C21H30O5, and methyl syn-1,3,3a,6,7,7a-tetrahydro-3-(1,1-dimethylethyl)-1-oxo-3a,6-epoxyisobenzofuran-7-carboxylate, C14H18O5, establish the configuration at the chiral centers and provide insights into the factors controlling the diastereomeric differentiation.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks global, II, V

fcf

Structure factor file (CIF format)
Contains datablock tb164

fcf

Structure factor file (CIF format)
Contains datablock V

CCDC references: 128571; 128572

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