The Journal of organic chemistry

Regioselective palladium-catalyzed formate reduction of N-heterocyclic allylic acetates

HY Cheng, CS Sun, DR Hou

Index: Cheng, Hsiu-Yi; Sun, Chong-Si; Hou, Duen-Ren Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2674 - 2677

Full Text: HTML

Citation Number: 17

Abstract

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.

Related Articles:

N??Heterocyclic Carbene and Phosphine Ruthenium Indenylidene Precatalysts: A Comparative Study in Olefin Metathesis

[Clavier, Herve; Nolan, Steven P. Chemistry - A European Journal, 2007 , vol. 13, # 28 p. 8029 - 8036]

Syntheses and Reactivity of Analogues of Grubbs' Second Generation Metathesis Catalyst with Fluorous Phosphines: A New Phase??Transfer Strategy for Catalyst …

[Da Costa, Rosenildo Correa; Gladysz, John A. Advanced Synthesis and Catalysis, 2007 , vol. 349, # 1-2 p. 243 - 254]

An Efficient, Overall [4+ 1] Cycloadditon of 1, 3??Dienes and Nitrene Precursors

[Wu, Qiong; Hu, Jian; Ren, Xinfeng; Zhou, Jianrong Chemistry - A European Journal, 2011 , vol. 17, # 41 p. 11553 - 11558]

Ring Size??Selective Ring??Closing Olefin Metathesis: Taking Advantage of the Deleterious Effect of Ethylene Gas

[Yoshida, Kazuhiro; Kano, Yuto; Takahashi, Hidetoshi; Yanagisawa, Akira Advanced Synthesis and Catalysis, 2011 , vol. 353, # 8 p. 1229 - 1233]

An Efficient, Overall [4+ 1] Cycloadditon of 1, 3??Dienes and Nitrene Precursors

[Wu, Qiong; Hu, Jian; Ren, Xinfeng; Zhou, Jianrong Chemistry - A European Journal, 2011 , vol. 17, # 41 p. 11553 - 11558]

More Articles...