title: From enantiopure hydroxyaldehydes to complex heterocyclic scaffolds: development of domino Petasis/Diels-Alder and cross-metathesis/Michael addition reactions.
abstract: One-step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono-Mannich) and Diels-Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is applicable to a broad range of substrates, including free sugars, and holds significant potential to efficiently and stereoselectively build new heterocyclic structures. This easy and fast entry to functionalized polycyclic compounds can be pursued by further transformations, for example, additional ring closure by a cross-metathesis/Michael addition domino sequence.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles du CNRS, CNRS UPR 2301 Avenue de la Terrasse, 91198 Gif-sur-Yvette (France), Fax: (+33) 169077247.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Cannillo
authors.forename: Stéphanie
authors.initials: S
authors.lastname: Norsikian
authors.forename: Marie-Elise
authors.initials: ME
authors.lastname: Tran Huu Dau
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Bogdan I
authors.initials: BI
authors.lastname: Iorga
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Beau
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D061565:Cycloaddition Reaction / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds
keywords: Diels-Alder reaction; borono-Mannich reaction; carbohydrates; domino reactions; metathesis