2016/01/28 by Siu Min Tan, Anthony C. Willis, Michael N. Paddon‐Row +1 · 1 citation
Chemistry · #Asymmetric Synthesis and Catalysis #Organic Chemistry Cycloaddition Reactions #Synthetic Organic Chemistry Methods
paper · pdf · doi:10.1002/anie.201510925
openalex publication_date 2016/01/28 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02
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.