ol6b03068_si_001.pdf (2.94 MB)
Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8‑endo-trig Nucleophilic Cyclization of Cyclopropenes
journal contribution
posted on 2016-12-02, 17:20 authored by Pavel Ryabchuk, Jonathon P. Matheny, Marina Rubina, Michael RubinAn
efficient approach toward enantioenriched eight-membered heterocycles
via the intramolecular formal substitution of bromocyclopropanes with
oxygen-based nucleophiles has been developed. The reaction proceeds
via a reactive cyclopropene intermediate, which undergoes a rapid
8-endo-trig cyclization affording cis-fused [6.1.0] bicyclic products exclusively. The quaternary chiral
center in the cyclopropene governs the configuration of the other
two stereocenters in the final product.
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bicyclicstereocenterCyclizationciintramolecularChiral Medium-Sized Cyclic Ethersbromocyclopropanequaternary chiral centerapproachTemplated AssemblyNucleophilicreaction proceedsoxygen-based nucleophilesenantioenriched eight-membered heterocycles8- endo-trig cyclizationsubstitutionreactive cyclopropeneconfigurationCyclopropene
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