Chiral polyfunctionalised cyclopentanes have been readily obtained in ~65% enantiomeric excess via a stereo-specific Wagner–Meerwein rearrangement induced by bromination of derivatives of the exo-cis Diels–Alder adduct of furan and maleic anhydride, combined with desymmetrisation of a meso intermediate by pig liver esterase.
References
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WoodwardR.B., and BaerH., J. Amer. Chem. Soc., 70, 1161 (1948).
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DielsO., and AlderK., Chem. Ber., 62, 554 (1929).
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Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 142201 for structure 7 and 142198 for structure 8.
