title: Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.
abstract: The synthesis and Diels-Alder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels-Alder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.
authors: Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
authors: Laural A
authors: LA
authors: Fisher
authors: Natalee J
authors: NJ
authors: Smith
authors: Joseph M
authors: JM
authors: Fox
mesh_terms: D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D003521:Cyclopropanes; D007659:Ketones