Rhenium(I)-Catalyzed Cyclopropanation of Alkenes with Vinylcarbenes Derived from Propargylic Ethers
Abstract
A rhenium-catalyzed method employing tetrahydropyran-substituted propargyl ethers as practical nondiazo carbene precursor for the efficient synthesis of vinylcyclopropanes (VCPs) is described. This method features a sequential 1,2-/1,5-hydride migration process to generate reactive vinyl rhenium carbenes, enabling subsequent cyclopropanation with a wide range of alkenes under user-friendly conditions. Notably, this operationally simple protocol features a broad substrate scope and provides a readily accessible starting material for assembling synthetically valuable VCPs. Furthermore, this method demonstrates significant potential in natural product synthesis.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Catalytic Alkyne Reactions
Organometallic Complex Synthesis and Catalysis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 10
- Pages
- 3871–3883
- Publication date
- 28 February 2026
- Language
- EN