Synthesis 2007(20): 3211-3218  
DOI: 10.1055/s-2007-990801
PAPER
© Georg Thieme Verlag Stuttgart · New York

[3+2] Cycloaddition of Phenyliodonium Bis(arylsulfonyl)methylides with α,β-Enones

Waldemar Adama,b, Efstathios P. Gogonasa,c, Ioannis A. Nyxasc, Lazaros P. Hadjiarapoglou*c
a Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
b Department of Chemistry, Facundo Bueso 110, University of Puerto Rico, Rio Piedras, Puerto Rico 00931, USA
c Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
Fax: +30(26510)98799; e-Mail: lxatziar@uoi.gr;
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Publikationsverlauf

Received 11 July 2007
Publikationsdatum:
21. September 2007 (online)

Abstract

The [3+2] cycloaddition of phenyliodonium bis(arylsulfonyl)methylides to α,β-enones affords exclusively trans,trans-configured 1-(arylsulfonyl)-2-aroyl-3-arylindanes. The initial electrophilic attack of the iodonium ylide on the alkenyl double bond of the chalcone, followed by cyclization of the dipolar species, and subsequent ejection of iodobenzene and sulfur dioxide, stereoselectively affords the indane cycloadduct.