Metal-mediated cross-coupling of activated enol-triflates and enol-carbamates

Date

2013

Authors

Still, Raymond S.

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Abstract

Two projects are discussed: The regioselective synthesis of pyrazoles and the stereoselective synthesis and use of enol carbamate esters. First, pyrazoles are generated by an initial palladium-catalyzed cross-coupling of stereodefined enol trilfate esters with diazoacetates, followed by a thermally induced 6pi-electrocyclization. Then, conditions to generate (E )-vinyl carbamates are developed, and literature preparations are used to synthesize (Z)-vinyl carbamates. Development of methodology to cross-couple these stereodefined enol carbamates with alkyl Grignard reagents to produce tri-and tetrasubstituted olefins using a Fe(III) precatalyst is presented.

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Department

Chemistry