Synthesis of Seven-Membered Carbocyclic Rings via a Microwave-Assisted Tandem Oxyanionic 5-exo dig Cyclization−Claisen Rearrangement Process

2007/07/27 by Xin Li, Robert E. Kyne, Timo V. Ovaska · 1 citation
Chemistry · #Catalytic Alkyne Reactions #Catalytic Cross-Coupling Reactions #Chemistry #Claisen rearrangement #Cyclopropane Reaction Mechanisms #Dig #Enone #Organic chemistry #Stereochemistry #Stereoselectivity #Tandem

paper · doi:10.1021/jo0710432

openalex publication_date 2007/07/27 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/26

Abstract

Appropriately substituted 1-alkenyl-4-pentyn-1-ol systems, readily prepared from simple starting materials, serve as useful precursors to a number of substituted cyclohept-4-enone derivatives via a microwave-assisted tandem oxyanionic 5-exo cyclization/Claisen rearrangement sequence. The reactions involving terminally substituted 4-pentyn-1-ols were found to be highly stereoselective, with the alpha and beta groups in the final product showing a strong preference for the trans orientation.

Citations

• Transition-Metal-Catalyzed Addition of Heteroatom−Hydrogen Bonds to Alkynes

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• Baldwin's rules [wikipedia]

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