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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)681-690
Number of pages10
JournalHeterocycles
Volume63
Issue number3
Publication statusPublished - 1 Mar 2004

Fingerprint Dive into the research topics of 'Diastereoselective synthesis of substituted 2-phenyltetrahydropyrans as useful precursors of aryl C-glycosides via selenoetherification'. Together they form a unique fingerprint.

  • Cite this