Versatile One-Pot Reductive Alkylation of Lactams/Amides via Amide Activation: Application to the Concise Syntheses of Bioactive Alkaloids (±)-Bgugaine, (±)-Coniine, (+)-Preussin, and (−)-Cassine

Versatile One-Pot Reductive Alkylation of Lactams/Amides via Amide Activation: Application to the Concise Syntheses of Bioactive Alkaloids (±)-Bgugaine, (±)-Coniine, (+)-Preussin, and (−)-Cassine

Direct entry: One‐pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α‐alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)‐bgugai...

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Veröffentlicht in:Chemistry : a European journal 2010-11, Vol.16 (43), p.12792-12796
Hauptverfasser: Xiao, Kai-Jiong, Wang, Yu, Ye, Ke-Yin, Huang, Pei-Qiang
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Alkaloids - chemical synthesis
Alkaloids - chemistry
Alkylation
amide activation
Amides - chemistry
Anisomycin - analogs & derivatives
Anisomycin - chemical synthesis
Anisomycin - chemistry
Chemistry
Combinatorial Chemistry Techniques
Ketones - chemical synthesis
Ketones - chemistry
Lactams - chemistry
Molecular Structure
Oxidation-Reduction
Piperidines - chemical synthesis
Piperidines - chemistry
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
reduction
Stereoisomerism
synthetic methods
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Zusammenfassung:Direct entry: One‐pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α‐alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)‐bgugaine, (±)‐coniine, (+)‐preussin, and (−)‐cassine.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201002054