Diastereoselective synthesis of substituted 2-phenyltetrahydropyrans as useful precursors of aryl C-glycosides via selenoetherification

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

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Résumé

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.

langue originaleAnglais
Pages (de - à)681-690
Nombre de pages10
journalHeterocycles
Volume63
Numéro de publication3
Etat de la publicationPublié - 1 mars 2004

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