A Stereoselective and Regioselective Synthesis of trans,trans-Configured 1,2,3-Trisubstituted Indanes: Cycloaddition of Alkenes with Iodonium Ylides of β-Disulfones

Waldemar  Adam; Sara G.  Bosio; Efstathios P.  Gogonas; Lazaros P.  Hadjiarapoglou

doi:10.1055/s-2002-34376

PAPER

A Stereoselective and Regioselective Synthesis of trans,trans-Configured 1,2,3-Trisubstituted Indanes: Cycloaddition of Alkenes with Iodonium Ylides of β-Disulfones

Waldemar Adam*^a, Sara G. Bosio^a, Efstathios P. Gogonas^a,b, Lazaros P. Hadjiarapoglou^b
^a Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
e-Mail: adam@chemie.uni-wuerzburg.de;
^b Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece

Abstract

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Abstract

The reaction of phenyliodonium-bis(sulfonyl) methylides α-γ 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.

Key words

cycloaddition - 1,2,3-trisubstituted indanes - iodonium ylides - diastereoselective synthesis

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