Ruthenium-Catalyzed One-Pot Tandem Isomerization-Transfer Hydrogenation Reactions of γ-Trifluoromethylated Allylic Alcohols and β-Trifluoromethylated Enones

被引:27
作者
Bizet, Vincent [1 ,2 ]
Pannecoucke, Xavier [1 ,2 ]
Renaud, Jean-Luc [3 ]
Cahard, Dominique [1 ,2 ]
机构
[1] Univ Mt St Aignan, COBRA, CNRS, UMR 6014, F-76821 Mont St Aignan, France
[2] INSA Rouen, F-76821 Mont St Aignan, France
[3] Univ Caen Basse Normandie, Normandie Univ, CNRS, Lab Chim Mol & Thioorgan,UMR 6507, F-14050 Caen, France
关键词
allylic compounds; enones; fluorine; isomerization; ruthenium; COMPLEXES; REDUCTION; FLUORINE; CARBENE; IRIDIUM; CHEMISTRY; SOLVENT; KETONES;
D O I
10.1002/adsc.201300119
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The ruthenium2-propanol combination was found to transform -trifluoromethylated allylic alcohols and -trifluoromethylated enones into the corresponding saturated alcohols in excellent yields via a one-pot tandem process involving isomerization and transfer hydrogenation(s). High stereospecificity was demonstrated and evidence for two mechanistic pathways is provided. The method was applied to a rapid synthesis of trifluoromethylated citronellol.
引用
收藏
页码:1394 / 1402
页数:9
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