Multicomponent Diene‐Transmissive Diels–Alder Sequences Featuring Aminodendralenes |
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| Authors: | Siu Min Tan Dr Anthony C Willis Prof Michael N Paddon‐Row Prof Michael S Sherburn |
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| Institution: | 1. Research School of Chemistry, Australian National University, Canberra, ACT, Australia;2. School of Chemistry, The University of New South Wales, Sydney, NSW, Australia |
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| 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. |
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| Keywords: | density functional calculations Diels– Alder reactions domino reactions multicomponent reactions polycycles |
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