California Institute of Technology

Kelly E Kim

Brian M Stoltz

Robert H Grubbs

Alexey Fedorov

Douglas Duquette

Yiyang Liu

Yoshitaka Numajiri

Alexander N Marziale

Robert A Craig

Marc Liniger

Yoshitaka Numajira

This invention provides efficient and scalable enantioselective methods that yield 2-alkyl-2-allylcycloalkyanone compounds with quaternary stereogenic centers. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II) or (III): with a palladium (II) catalyst under alkylation conditions.

Asymmetric catalytic decarboxylative alkyl alkylation using low catalyst concentrations and a robust precatalyst

The present invention is directed to methods of forming olefins, especially linear alpha olefins from fatty acids or anhydrides, each method comprising: contacting an amount of precursor carboxylic acid anhydride with a palladium catalyst comprising a bidentate bis-phosphine ligand in a reaction mixture so as to form an olefin in a product with the concomittant formation and removal of CO and water from the reaction mixture, either directly or indirectly, wherein the reaction mixture is maintained with a sub-stoichiometric excess of a sacrificial carboxylic acid anhydride, an organic acid, or both, said sub-stoichiometric excess being relative to the amount of the precursor carboxylic acid anhydride. The precursor carboxylic acid anhydride may be added to the reaction mixture directly or formed in situ by the reaction between at least one precursor carboxylic acid with a stoichiometric amount of the sacrificial acid anhydride.

Palladium-catalyzed decarbonylation of fatty acid anhydrides for the production of linear alpha olefins

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Pasadena, CA, United States of America

Kelly E Kim