Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes

Crowley, Patrick J and Fawcett, John and Kariuki, Benson M and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2002) Basic and reductive sulfone-directed ring-opening reactions of difluorinated oxa[2.2.1]bicycloheptanes. Organic Letters, 4 (23). pp. 4125-4128. ISSN 1523-7060 (https://doi.org/10.1021/ol0268743)

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Abstract

Phenylsulfenyl chloride reacts with racemic endo Diels-Alder adduct 4 (DEC ) CONEt2) to afford lactone 8, which can be reduced and protected in a series of high-yielding steps. Key sulfone 10 can be ring opened under strong base conditions to afford vinyl sulfone 11. Attempted desulfonation resulted in the formation of a monofluoroalkene, but a direct desulfonation/eliminative ring opening with strain relief delivered highly functionalized monocyclic species 16.

ORCID iDs

Crowley, Patrick J, Fawcett, John, Kariuki, Benson M, Moralee, Andrew C, Percy, Jonathan ORCID logoORCID: https://orcid.org/0000-0001-8636-2704 and Salafia, Vittoria;
CORE (COnnecting REpositories)