Stereoselective Synthesis of 2,4,5-Trisubstituted Tetrahydropyrans using an Intramolecular Allylation Strategy

Peter Jervis, Benson Kariuki, Liam Cox

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

A highly stereoselective route to 2,4,5-trisubstituted tetrahydropyrans is reported. The key step employs an intramolecular allylation of a (Z)-allylsilane onto an aldehyde under Bronsted acid activation. Complete 1,4-stereoinduction accounts for the formation of only two out of the possible four THP products. The level of 1,3-stereoinduction is optimal when the reaction is carried out in an apolar solvent, which is in accord with electrostatics being key to controlling this aspect of the stereoselectivity.
Original languageEnglish
Pages (from-to)4649-4652
Number of pages4
JournalOrganic Letters
Volume8
DOIs
Publication statusPublished - 28 Sep 2006

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