title: Silver-Catalyzed 1,3-Acyloxy Migration/Diels-Alder Reaction of 1,9-Dien-4-yne Esters to Partially Hydrogenated Isoquinolines.
abstract: A synthetic method to prepare partially hydrogenated isoquinolines efficiently from silver-mediated [3,3]-sigmatropic rearrangement/Diels-Alder reaction of 1,9-dien-4-yne esters is described. The reactions were shown to be robust with a wide variety of substitution patterns tolerated to provide the corresponding nitrogen-containing heterocyclic products in good to excellent yields. This includes examples containing a bridgehead sp3quaternary carbon center as well as the cycloisomerization of one substrate to give the corresponding bicyclic adduct in excellent yield at the gram scale.
authors.affiliation: School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.
authors.forename: Yichao
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.
authors.forename: Jianwen
authors.initials: J
authors.lastname: Jin
authors.affiliation: School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.
authors.forename: Joshua William
authors.initials: JW
authors.lastname: Boyle
authors.affiliation: School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.
authors.forename: Bo Ra
authors.initials: BR
authors.lastname: Lee
authors.affiliation: Department of Chemistry, University of Warwick , Coventry CV4 7AL, United Kingdom.
authors.forename: David Philip
authors.initials: DP
authors.lastname: Day
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
authors.forename: Dewi
authors.initials: D
authors.lastname: Susanti
authors.affiliation: Department of Chemistry, University of Warwick , Coventry CV4 7AL, United Kingdom.
authors.forename: Guy James
authors.initials: GJ
authors.lastname: Clarkson
authors.affiliation: School of Chemistry, Monash University , Clayton, Victoria 3800, Australia.|Department of Chemistry, University of Warwick , Coventry CV4 7AL, United Kingdom.
authors.forename: Philip Wai Hong
authors.identifier: 0000-0002-8786-6143
authors.initials: PW
authors.lastname: Chan