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.

SUBMITTER: Fisher LA 

PROVIDER: S-EPMC3908886 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature