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Chiral Cyclopropenyl Ketones: Reactive and Selective Diels–Alder Dienophiles

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posted on 2013-04-05, 00:00 authored by Laural A. Fisher, Natalee J. Smith, Joseph M. Fox
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.