A short stereoselective synthesis of (+)- and (-)-2-oxabicyclo[3.3.0]oct-6-en-3-one by intramolecular carbon-hydrogen insertion catalyzed by chiral dirhodium(II) carboxamidates

Article abstract of DOI:10.1016/S0957-4166(03)00083-1

The synthesis of (1S,5R)-(-)-2-oxabicyclo[3.3.0]oct-6-en-3-one, a useful synthetic precursor en route to various prostaglandins, from divinylcarbinol via catalytic metathesis and C-H insertion of 3-cyclopentenyl diazoacetate is described. Enantioselectivities of 90±1% have been achieved in the insertion process.