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Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns.

ABSTRACT: Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels-Alder cycloadditions. We have found 2-brominated cycloalkenone dienophiles to be both highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cyclopropyl functional handles is described.

SUBMITTER: Ross AG

PROVIDER: S-EPMC3543988 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns.

Ross Audrey G AG Townsend Steven D SD Danishefsky Samuel J SJ

The Journal of organic chemistry 20121127 1

Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels-Alder cycloadditions. We have found 2-brominated cycloalkenone dienophiles to be both highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cyclopropyl functional handles is described. ...[more]

PMID: 23151095

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