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Multicomponent Diene‐Transmissive Diels–Alder Sequences Featuring Aminodendralenes
Author(s) -
Tan Siu Min,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510925
Subject(s) - diene , enamine , chemistry , diels–alder reaction , amine gas treating , computational chemistry , density functional theory , organic chemistry , combinatorial chemistry , catalysis , natural rubber
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.