title: Synthesis of amino-substituted indanes and tetralins via consecutive multibond-forming tandem processes.
abstract: A rapid and general approach for the synthesis of amino-substituted indanes and tetralins from readily available alkyne-derived allylic alcohols via consecutive multibond-forming tandem processes has been developed. In the first one-pot tandem process, a series of cyclic dienes were prepared using an Overman rearrangement under thermal conditions, followed by a ruthenium(II)-catalyzed ring closing enyne metathesis reaction. The resulting exo-dienes were then subjected to a second one-pot tandem process involving a highly regioselective Diels-Alder reaction with alkynes, quinones or nitriles and a subsequent oxidation step to give a diverse library of C-1 amino-substituted indanes and tetralins in good overall yields.
authors.affiliation: WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, United Kingdom.
authors.forename: Mark W
authors.initials: MW
authors.lastname: Grafton
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Farrugia
authors.forename: Andrew
authors.initials: A
authors.lastname: Sutherland
mesh_terms: D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007189:Indans; D020005:Propanols; D013764:Tetrahydronaphthalenes; C006463:allyl alcohol