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Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes

Tan, Siu Min; Willis, Anthony C; Paddon-Row, Michael N; Sherburn, Michael


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...[Show more]

CollectionsANU Research Publications
Date published: 2016-02-24
Type: Journal article
Source: Angewandte Chemie (International ed. in English)
DOI: 10.1002/anie.201510925
Access Rights: Open Access


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