2009/12/11 by Tanya A. Bradford, Alan D. Payne, Anthony C. Willis +2 · 5 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Axial and Atropisomeric Chirality Synthesis #Inorganic and Organometallic Chemistry
paper · doi:10.1021/jo9024557
openalex publication_date 2009/12/11 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02
A convenient and high-yielding three-step synthesis of the simplest branched triene, [3]dendralene, has been devised. The synthesis is robust and operationally simple, requiring no chromatography and involving no protecting groups or specialized equipment, allowing the synthesis of the volatile hydrocarbon in pure, solvent free form on a multigram scale. The stability, dimerization when stored neat, and Diels-Alder reactivity of [3]dendralene--including double cycloaddition sequences and catalytic enantioselective variant--are reported.