Multicomponent Diene-Transmissive Diels-Alder Sequences Featuring Aminodendralenes

• Published in: Angewandte Chemie International Edition Vol. 55; no. 9; pp. 3081 - 3085
• Main Authors: Tan, Siu Min, Willis, Anthony C., Paddon-Row, Michael N., Sherburn, Michael S.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 24.02.2016; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Ambient temperature; Chemical bonds; Chemistry; Chemistry, Multidisciplinary; Density; density functional calculations; Density functional theory; Diels-Alder reactions; domino reactions; Functional anatomy; Mathematical analysis; multicomponent reactions; Physical Sciences; polycycles; Science & Technology; Temperature effects; Diels-Alder reactions; density functional calculations; multicomponent reactions; CATALYSIS; domino reactions; CYCLOADDITIONS; REMOTE FUNCTIONALIZATION; ORGANOCATALYSIS; ENAMINES; polycycles
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201510925

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. Amine way to make polycycles: Multicyclic amine‐containing systems are accessible in one‐pot sequences from a skipped dienal, an amine, and two dienophiles. This stereoselective and atom‐economical method delivers five new covalent bonds, and is brought about simply by mixing the precursors.