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Note | Regular issue | Vol 63, No. 3, 2004, pp.681-690
Published online, 19th January, 2004
DOI: 10.3987/COM-03-9959
Diastereoselective Synthesis of Substituted 2-Phenyltetrahydropyrans as Useful Precursors of Aryl C-Glycosides via Selenoetherification

Michelangelo Gruttadauria,* Carmela Aprile, Paolo Lo Meo, Serena Riela, and Renato Noto

*Department of Organic Chemistry "E. Paternò", University of Palermo, Viale delle Scienze, Parco d'Orleans II, 90128 Palermo, Italy


The cyclization of several substituted 5-phenyl-pent-4-en-1-ols with selenium electrophiles along some mechanistic considerations is discussed. In particular, an efficient diastereoselective synthesis of a 2,3,5,6-tetrasubstitued tetrahydropyran is reported. These findings open an interesting approach: the use of chiral selenium electrophiles for cyclization of chiral substrates. The cyclized products are useful starting material for the synthesis of D- or L-aryl C-glycosides.