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Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp(3))-H bonds. | LitMetric
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Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp(3))-H bonds.

Gang He Shu-Yu Zhang William A Nack Qiong Li Gong Chen

Angew Chem Int Ed Engl

Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA).

Published: October 2013

Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp(3) )H and C(sp(2) )H bonds of secondary amides included 5-methoxy-8-aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β-CH methylation or γ-CH arylation step, the γ-C(sp(3) )H amination provided access to complex pyrrolidones from readily available precursors.

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http://dx.doi.org/10.1002/anie.201305615DOI Listing

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