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A Facile Diastereoselective Synthesis of Functionalized 1,2,3-Trisubstituted Benzocyclopentenes through the Cycloaddition of Bis(phenylsulfonyl)iodonium Ylides to Cyclic Alkenes

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journal contribution
posted on 14.11.2003, 00:00 by Waldemar Adam, Efstathios P. Gogonas, Lazaros P. Hadjiarapoglou
The thermal cycloaddition of β-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo[3.3.0]octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.

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