title: Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.
abstract: Stereodivergent metallacycle-mediated cross-coupling reactions are described for the synthesis of densely functionalized vinylcyclopropanes from the union of alkynes with cyclopropenes. Strategies explored include hydroxyl-directed and nondirected processes, with the latter of these delivering vinylcyclopropanes with exquisite levels of regio- and stereoselectivity. Challenges inherent to these coupling reactions include diastereoselectivity (with respect to the cyclopropene) and regioselectivity (with respect to both coupling partners).
authors.affiliation: Department of Chemistry, Burke Laboratory, Dartmouth College , Hanover, New Hampshire 03755, United States.
authors.forename: Natasha F
authors.initials: NF
authors.lastname: O'Rourke
authors.affiliation: Department of Chemistry, Burke Laboratory, Dartmouth College , Hanover, New Hampshire 03755, United States.
authors.forename: Glenn C
authors.initials: GC
authors.lastname: Micalizio
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D003521:Cyclopropanes; D014753:Vinyl Compounds; C021985:cyclopropene