Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)H Bonds

Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)H Bonds

Easy on, easy off: Directing groups found to promote the palladium‐catalyzed amination of γ C(sp3)H and C(sp2)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 methylatio...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-10, Vol.52 (42), p.11124-11128
Hauptverfasser: He, Gang, Zhang, Shu-Yu, Nack, William A., Li, Qiong, Chen, Gong
Format: Artikel
Sprache:eng
Schlagworte:
Amination
auxiliary groups
CH amination
Molecular Structure
palladium
Palladium - chemistry
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
pyrrolidones
Stereoisomerism
γ-lactams
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Beschreibung
Zusammenfassung:Easy on, easy off: Directing groups found to promote the palladium‐catalyzed amination of γ C(sp3)H and C(sp2)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(sp3)H amination provided access to complex pyrrolidones from readily available precursors.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201305615