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Synthesis 2002(7): 0958-0972
DOI: 10.1055/s-2002-28506
DOI: 10.1055/s-2002-28506
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Tandem Ene-Reaction/Intramolecular Sakurai Cyclisation (IMSC): A Novel Access to Polysubstituted Tetrahydropyrans and γ-Butyrolactones Using a Unique Allylation Strategy
Further Information
Received
11 April 2002
Publication Date:
14 May 2002 (online)
Publication History
Publication Date:
14 May 2002 (online)
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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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