title: Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes.
abstract: 1-Aminodecalins were prepared from acyclic precursors by combining the powerful twofold diene-transmissive Diels-Alder chemistry of [3]dendralenes with the simplicity of enamine formation. On mixing at ambient temperature, a simple dienal condenses with a primary or secondary amine to generate the enamine, a 1-amino-[3]dendralene in situ, and this participates as a double diene in a sequence of two Diels-Alder events with separate dienophiles. Overall, four C-C bonds and one C-N bond are formed. Mechanistic insights into these reactions are provided by means of density functional theory calculations.
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, 0200, Australia.
authors.forename: Siu Min
authors.initials: SM
authors.lastname: Tan
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, 0200, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
authors.affiliation: School of Chemistry, The University of New South Wales, Sydney, NSW, 2052, Australia. m.paddonrow@unsw.edu.au.
authors.forename: Michael N
authors.initials: MN
authors.lastname: Paddon-Row
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT, 0200, Australia. michael.sherburn@anu.edu.au.
authors.forename: Michael S
authors.identifier: http://orcid.org/0000-0001-5098-0703
authors.initials: MS
authors.lastname: Sherburn
keywords: Diels-Alder reactions; density functional calculations; domino reactions; multicomponent reactions; polycycles