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General route for preparing ?-nitrocarbonyl compounds using copper thermal redox catalysis.

ABSTRACT: Using a simple copper catalyst, the alkylation of nitroalkanes with ?-bromocarbonyls is now possible. This method provides a general, functional group tolerant route to ?-nitrocarbonyl compounds, including nitro amides, esters, ketones, and aldehydes. The highly sterically dense, functional group rich products from these reactions can be readily elaborated into a range of complex nitrogen-containing molecules, including highly substituted ?-amino acids.

SUBMITTER: Gietter AA

PROVIDER: S-EPMC4051431 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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General route for preparing β-nitrocarbonyl compounds using copper thermal redox catalysis.

Gietter Amber A S AA Gildner Peter G PG Cinderella Andrew P AP Watson Donald A DA

Organic letters 20140528 11

Using a simple copper catalyst, the alkylation of nitroalkanes with α-bromocarbonyls is now possible. This method provides a general, functional group tolerant route to β-nitrocarbonyl compounds, including nitro amides, esters, ketones, and aldehydes. The highly sterically dense, functional group rich products from these reactions can be readily elaborated into a range of complex nitrogen-containing molecules, including highly substituted β-amino acids. ...[more]

PMID: 24870052

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