Highly Enantioselective Hydrogenation of Aryl Vinyl Ketones to Allylic Alcohols Catalyzed by the Tol-Binap/Dmapen Ruthenium(II) Complex

Highly Enantioselective Hydrogenation of Aryl Vinyl Ketones to Allylic Alcohols Catalyzed by the Tol-Binap/Dmapen Ruthenium(II) Complex

Binap catalyst doesn't dmapen expectations: In basified 2‐propanol, [RuCl2{(S)‐tol‐binap}{(R)‐dmapen}] (1, see picture, Ar=4‐CH3C6H4) 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. Formati...

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Veröffentlicht in:Angewandte Chemie International Edition 2008-09, Vol.47 (39), p.7457-7460
Hauptverfasser: Arai, Noriyoshi, Azuma, Keita, Nii, Noriyuki, Ohkuma, Takeshi
Format: Artikel
Sprache:eng
Schlagworte:
allylic compounds
asymmetric catalysis
hydrogenation
ketones
ruthenium
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Zusammenfassung:Binap catalyst doesn't dmapen expectations: In basified 2‐propanol, [RuCl2{(S)‐tol‐binap}{(R)‐dmapen}] (1, see picture, Ar=4‐CH3C6H4) 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802533