Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates

Regioselective Palladium-Catalyzed Formate Reduction of N-Heterocyclic Allylic Acetates

The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in...

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Veröffentlicht in:Journal of organic chemistry 2007-03, Vol.72 (7), p.2674-2677
Hauptverfasser: Cheng, Hsiu-Yi, Sun, Chong-Si, Hou, Duen-Ren
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Zusammenfassung:The regioselective palladium-catalyzed formate reduction of allylic acetates in five- to eight-membered heterocycles is reported. Reduction of allylic acetates under mild conditions using allylpalladium chloride dimer, phosphines, and formic acid/triethylamine in DMF gives the exo-cyclic olefins in good regioselectivities and high yields. Synthetic application in preparing N-tosyl-3-oxo-piperidine is also reported.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0624896