title: Templated Assembly of Chiral Medium-Sized Cyclic Ethers via 8-endo-trig Nucleophilic Cyclization of Cyclopropenes.
abstract: An 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.
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Leibniz-Institut für Katalyse e.V. an der Universität Rostock , Albert-Einstein Straße 29a, Rostock 18059, Germany.
authors.forename: Pavel
authors.initials: P
authors.lastname: Ryabchuk
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
authors.forename: Jonathon P
authors.initials: JP
authors.lastname: Matheny
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
authors.forename: Marina
authors.initials: M
authors.lastname: Rubina
authors.affiliation: Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.|Department of Chemistry, North Caucasus Federal University , 1a Pushkin St., Stavropol 355009, Russian Federation.
authors.forename: Michael
authors.identifier: 0000-0002-1668-9311
authors.initials: M
authors.lastname: Rubin
mesh_terms: D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D010316:Particle Size
chemical_list: D003521:Cyclopropanes; D004988:Ethers, Cyclic; C021985:cyclopropene