Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions

2011/01/01 by Rekha Singh, Sunil K. Ghosh · 1 citation
Chemistry · #Advanced Synthetic Organic Chemistry #Asymmetric Synthesis and Catalysis #Phosphorus compounds and reactions

paper · doi:10.1039/c1cc14211a

openalex publication_date 2011/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30

Abstract

Dimethylsulfonium methylide mediated olefination of 2-phenylethenylidene phosphonoacetate followed by the Horner-Wadsworth-Emmons reaction with aromatic aldehydes provided access to reactive 1,5-diaryl-2-ethoxycarbonyl [3]dendralenes which in situ underwent Diels-Alder cyclodimerisation leading to highly functionalised cyclohexenes with very high regio- and stereoselectivity.

Citations

• Efficient ruthenium-catalyzed synthesis of [3]dendralenes from 1,3-dienic allylic carbonates
• Synthesis of cross-conjugated trienes by dimerization of allenes with palladium-phenol catalyst
• Practical Synthesis and Reactivity of [3]Dendralene
• Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior

Cited by

• Dendralene [wikipedia]

Related

• Synthesis and Diels–Alder Reactivity of Substituted [4]Dendralenes
• Practical Synthesis and Reactivity of [3]Dendralene
• Practical Synthesis of the Dendralene Family Reveals Alternation in Behavior
• Preparation and Synthetic Value of π-Bond-Rich Branched Hydrocarbons
• Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes