S y n t h e s i s o f t r a n s , t r a n s -C o n f i g u r e d 1 , 2 , 3 -T r i s u b s t i t u t e d I n d a n e s Abstract: The reaction of phenyliodonium-bis(sulfonyl) methylides a-g with alkenes 1 affords the multiply trisubstituted indanes 2 in moderate to good yields, through an unusual cycloaddition. The present stereoselective and regioselective cycloaddition provides a convenient preparative route to trans,trans-configured 1,2,3-trisubstituted indanes, in which the benzene ring derives from the arenesulfonyl functionality of the bis(sulfonyl)iodonium ylide. The mechanistically puzzling structural feature is the fact (X-ray structure) that the para-methyl substituent of the original p-toluenesulfonyl group in the iodonium ylide is located in the C-6 position of the resulting indane benzene ring, that is, a meta relationship with respect to the original methylide carbon atom.
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.
The thermal-catalyzed or photochemical reaction of iodonium ylides with pyrroles yields exclusively alpha-substituted pyrroles in moderate to good yields. [reaction: see text]
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