A stereoselective and regioselective synthesis of trans,trans-configured 1,2,3-trisubstituted indanes: Cycloaddition of alkenes with iodonium ylides of beta-disulfones
A stereoselective and regioselective synthesis of trans,trans-configured 1,2,3-trisubstituted indanes: Cycloaddition of alkenes with iodonium ylides of beta-disulfones
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Adam, W.
(EN)
Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
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Adam, W.
(EN)
The reaction of phenyliodonium-bis(sulfonyl) methylides alpha-gamma 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 arene-sulfonyl 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.
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