Tandem Ene-Reaction/Intramolecular Sakurai Cyclisation (IMSC): A Novel Access to Polysubstituted Tetrahydropyrans and γ-Butyrolactones Using a Unique Allylation Strategy

Abstract

The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of γ-butyrolactones and α-methylene-γ-butyrolactones.

Key words

ene-reactions - tetrahydropyrans - allylations - γ-butyrolactones - α-methylene-γ-butyrolactones

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