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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

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Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.

Fisher Laural A LA Smith Natalee J NJ Fox Joseph M JM

The Journal of organic chemistry 20130311 7

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. ...[more]

PMID: 23438063

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