The ‘racemate’1A/1B cyclises on heating to the enol 5via an ‘ene’ reaction; at two-thirds completion, the recovered enone 1A/1B has [α]D–62°(1B has [α]D–132°); kinetic ‘resolution’ results from a deuterium isotope effect for the cyclisation (kH/kDca. 1.8); the absolute stereochemistry of compound 6a is determined by X-ray analysis.
P. Anastasis, R. Duffin, C. Gilmore and K. Overton, J. Chem. Soc., Chem. Commun., 1991, 801 DOI: 10.1039/C39910000801
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