title: Access to polyfunctionalized diquinanes, hydrindanes, and decalines via TiCl4 promoted Michael-aldol and Baylis-Hillman reactions.
abstract: The addition of 0.5 equiv of TiCl(4) to (cyclo)alkanones tethered to α,β-unsaturated ketones afforded polyfunctionalized diquinanes, hydrindanes, and decalines. These products, resulting from a Michael-aldol or a Baylis-Hillman reaction, can be obtained with high or total diastereoselectivity in moderate to high yields. These scaffolds represent interesting building blocks for the synthesis of complex natural products.
authors.affiliation: Université de Strasbourg, Institut de Chimie, UMR UdS-CNRS 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP296/R8 67008, Strasbourg, France.
authors.forename: Blandine
authors.initials: B
authors.lastname: Ressault
authors.forename: Alexis
authors.initials: A
authors.lastname: Jaunet
authors.forename: Philippe
authors.initials: P
authors.lastname: Geoffroy
authors.forename: Sébastien
authors.initials: S
authors.lastname: Goudedranche
authors.forename: Michel
authors.initials: M
authors.lastname: Miesch
mesh_terms: D001688:Biological Products / Q000737:chemistry; D007189:Indans / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D007773:Lactates / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D001688:Biological Products; D007189:Indans; D007659:Ketones; D007773:Lactates; D009281:Naphthalenes; C531997:hydrindane; C007229:decalin; C025096:titanium tetrachloride; D014025:Titanium