Ruthenium‐Catalyzed One‐Pot Tandem Isomerization–Transfer Hydrogenation Reactions of γ‐Trifluoromethylated Allylic Alcohols and β‐Trifluoromethylated Enones | Zendy

Bizet Vincent | Zendy; Pannecoucke Xavier | Zendy; Renaud JeanLuc | Zendy; Cahard Dominique | Zendy

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

Author(s) -

Bizet Vincent,

Pannecoucke Xavier,

Renaud JeanLuc,

Cahard Dominique

Publication year - 2013

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201300119

Subject(s) - chemistry , isomerization , allylic rearrangement , ruthenium , transfer hydrogenation , tandem , catalysis , organic chemistry , stereospecificity , medicinal chemistry , combinatorial chemistry , materials science , composite material

The ruthenium–2‐propanol combination was found to transform γ‐trifluoromethylated allylic alcohols and β‐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.

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