Abstract
In the presence of catalytic quantities of [MoO 2Cl 2L] (L=β-ketophosphonate derived from camphor), water initiates the selective ring opening of cis (+) or (−)-limonene oxide to give the trans-diaxial diol. The trans isomer of the limonene oxide remains almost completely unreacted, thus providing a method for the kinetic separation of the trans diastereomer. 1H and 13C NMR studies of the interaction of the epoxide with the molybdenum complex show that the metal coordinates to the epoxide oxygen atom and that the diastereo-discriminating step is attack of MoO onto the tertiary carbocation formed by cleavage of a C–O bond in the epoxide.
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