A facile diastereoselective synthesis of functionalized 1,2,3-trisubstituted benzocyclopentenes through the cycloaddition of bis(phenylsulfonyl)iodonium ylides to cyclic alkenes
A facile diastereoselective synthesis of functionalized 1,2,3-trisubstituted benzocyclopentenes through the cycloaddition of bis(phenylsulfonyl)iodonium ylides to cyclic alkenes
(EN)
Adam, W.
(EN)
Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
(EL)
Adam, W.
(EN)
The thermal cycloaddition of beta-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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