title: Seebach's conjunctive reagent enables double cyclizations.
abstract: When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.
authors.affiliation: Department of Chemistry, Princeton University, Frick Chemical Laboratory, Princeton, New Jersey 08544, USA.
authors.forename: Brent D
authors.initials: BD
authors.lastname: Chandler
authors.forename: Jason T
authors.initials: JT
authors.lastname: Roland
authors.forename: Yukai
authors.initials: Y
authors.lastname: Li
authors.forename: Erik J
authors.initials: EJ
authors.lastname: Sorensen
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007659:Ketones; C503673:citrinadin A