Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes
Date
2016-02-24
Authors
Tan, Siu Min
Willis, Anthony C
Paddon-Row, Michael N
Sherburn, Michael
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
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.
Description
Keywords
diels-alder reactions, density functional calculations, domino reactions, multicomponent reactions, polycycles
Citation
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Source
Angewandte Chemie (International ed. in English)
Type
Journal article
Book Title
Entity type
Access Statement
Open Access