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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.