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Highly Enantioselective Hydrogenation of Aryl Vinyl Ketones to Allylic Alcohols Catalyzed by the Tol‐Binap/Dmapen Ruthenium(II) Complex
Author(s) -
Arai Noriyoshi,
Azuma Keita,
Nii Noriyuki,
Ohkuma Takeshi
Publication year - 2008
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/anie.200802533
Subject(s) - enantioselective synthesis , ruthenium , binap , allylic rearrangement , chemistry , aryl , catalysis , organic chemistry , noyori asymmetric hydrogenation , ketone , medicinal chemistry , alkyl
Binap catalyst doesn't dmapen expectations : In basified 2‐propanol, [RuCl 2 {( S )‐tol‐binap}{( R )‐dmapen}] ( 1 , see picture, Ar=4‐CH 3 C 6 H 4 ) catalyzes the highly enantioselective hydrogenation of a series of aryl vinyl ketones and affords the allylic alcohols in high yields with up to 98 % ee. Formation of the saturated ketones and alcohols is suppressed with triphenylphosphine when necessary.