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Novel Catalytic Hydrogenolysis of Trimethylsilyl Enol Ethers by the Use of an Acidic Ruthenium Dihydrogen Complex
Author(s) -
Nishibayashi Yoshiaki,
Takei Izuru,
Hidai Masanobu
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19991018)38:20<3047::aid-anie3047>3.0.co;2-f
Subject(s) - enol , hydrogenolysis , chemistry , ruthenium , ketone , heterolysis , trimethylsilyl , protonation , catalysis , trimethylsilyl trifluoromethanesulfonate , medicinal chemistry , nitrile , trifluoromethanesulfonate , organic chemistry , ion
The heterolytic cleavage of H 2 is the key to the novel catalytic hydrogenolysis of trimethylsilyl enol ethers catalyzed by [RuCl( η 2 ‐H 2 )(dppe) 2 ]OTf (dppe = 1,2‐bis(diphenylphosphanyl)ethane, OTf = trifluoromethanesulfonate), which results in the formation of a ketone and Me 3 SiH (see scheme). In addition, the stoichiometric, ruthenium‐assisted protonation of a prochiral lithium enolate with H 2 gave a chiral ketone with high enantioselectivity (up to 75 % ee ).