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Tandem ene-reaction/intramolecular Sakurai Cyclisation (IMSC): A novel access to polysubstituted tetrahydropyrans and gamma-butyrolactones using a unique allylation strategy

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Marko, Istvan [UCL] Dumeunier, R Leclercq, Cédric [UCL] Leroy, Bernard [UCL] Plancher, JM Bayston, DJ.

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 gamma-butyrolactones and alpha-methylene-gamma-butyrolactones.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2002
Language Anglais
Journal information "Synthesis : journal of synthetic organic chemistry" - , no. 7, p. 958-972 (2002)
Peer reviewed yes
Publisher Georg Thieme Verlag Kg (Stuttgart)
issn 0039-7881
e-issn 1437-210X
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords ene-reactions ; tetrahydropyrans ; allylations ; gamma-butyrolactones ; alpha-methylene-gamma-butyrolactones
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Bibliographic reference Marko, Istvan ; Dumeunier, R ; Leclercq, Cédric ; Leroy, Bernard ; Plancher, JM ; et. al. Tandem ene-reaction/intramolecular Sakurai Cyclisation (IMSC): A novel access to polysubstituted tetrahydropyrans and gamma-butyrolactones using a unique allylation strategy. In: Synthesis : journal of synthetic organic chemistry, , no. 7, p. 958-972 (2002)
Permanent URL http://hdl.handle.net/2078.1/41908