Synthesis of methyl 2-exo-cyano-3-exo-phenyl-5,6-endo (or exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates in enantiomerically pure form.

Add time:07/16/2019    Source:sciencedirect.com

The enantiomers (1R, 2R, 3S, 4S, 5S, 6S) and (1S, 2S, 3R, 4R, 5R, 6R) of the 2-exo-cyano-6-endo-hydroxy-5-exo-iodo-3-exo-phenylbicyclo[2.2.1]heptane-2-endo-carboxylic acid lactone 4 and 5, obtained starting from the endo-cycloadducts of the asymmetric Diels-Alder reactions between cyclopentadiene and (E)-2-cyanocinnamates of (R)-pantolactone 2 and (S)-ethyl lactate 3, are converted into the methyl 2-exo-cyano-3-exo-phenyl-5,6-endo(and exo)-epoxybicyclo[2.2.1]heptane-2-endo-carboxylates 6, 7, 8 and 9 in enantiomerically pure form.

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