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?-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

ABSTRACT: ?-Aminations of ketone-derived nitrones have been developed via [3,3]-rearrangement of the intermediates generated upon condensation with imidoyl chlorides. Careful reagent selection provides synthetically attractive amino protecting groups. The enediamide or ?'-carbamoyl enamide products can be hydrolyzed to the desired carbonyl, or exposed to electrophiles for further ?-functionalization.

SUBMITTER: Malinowski JT

PROVIDER: S-EPMC3545407 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

Malinowski Justin T JT Malow Ericka J EJ Johnson Jeffrey S JS

Chemical communications (Cambridge, England) 20120626 61

α-Aminations of ketone-derived nitrones have been developed via [3,3]-rearrangement of the intermediates generated upon condensation with imidoyl chlorides. Careful reagent selection provides synthetically attractive amino protecting groups. The enediamide or α'-carbamoyl enamide products can be hydrolyzed to the desired carbonyl, or exposed to electrophiles for further α-functionalization. ...[more]

PMID: 22733086

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