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

Autor:	Daniel J. Bayston, Raphael Dumeunier, István E. Markó, Jean-Marc Plancher, Cedric Leclercq, Abdelaziz Mekhalfia, Bernard Leroy
Rok vydání:	2002
Předmět:	chemistry.chemical_compound chemistry Tandem Stereochemistry Intramolecular force Organic Chemistry Tetrahydropyran Catalysis Ene reaction Adduct
Zdroj:	Synthesis. 2002:958-972
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2002-28506
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8b1d91149dce521ec6188de727db10f2 https://doi.org/10.1055/s-2002-28506 Zobrazit plný text záznamu