title: Ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts.
abstract: Strained nitroso Diels-Alder bicyclo[2.2.1] or [2.2.2] adducts functionalized with alkene side chains of diverse length undergo a ring-rearrangement metathesis process with external alkenes and Grubbs II or Hoveyda-Grubbs II ruthenium catalysts, under microwave irradiation or classical heating, to deliver cis-fused bicycles of various ring sizes, which contain a N-O bond. These scaffolds are of synthetic relevance for the generation of molecular diversity and to the total synthesis of alkaloids. The observation of unexpected reactions, such as epimerization or one-carbon homologation of the alkene side chain, is also reported.
authors.affiliation: Université Paris-Sud XI, Institut de Chimie Moléculaire et des Matériaux d'Orsay, UMR 8182, Laboratoire de Chimie des Procédés et Substances Naturelles, Orsay, 91405, France. guillaume.vincent@u-psud.fr
authors.forename: Guillaume
authors.initials: G
authors.lastname: Vincent
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky