ChemInform Abstract: Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)] (BF4) as a Catalyst Precursor for Enantioselective Hydrogenations.
✍ Scribed by Christopher J. A. Daley; J. A. Wiles; S. H. Bergens
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 43 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C 8 H 11 )] (BF 4 ) as a Catalyst Precursor for Enantioselective Hydrogenations.
-The title catalyst precursor forms under hydrogenation conditions in MeOH or acetone complexes containing the [Ru((R)-BINAP)(H)] + fragment. It acts as catalyst in the hydrogenation of α,β-unsaturated carboxylic acids or esters (I) and (III), 1,4-dicarboxylates (V) and (XI) with prochiral olefin or keto groups at the 2-position, allylic alcohol (VII), and ketone (IX) in MeOH or acetone as model for protic and aprotic solvents. The hydrogenation of the acids (Ia) and (Va) requires stoichiometric quantities of Et 3 N to occur in acetone. The enantioselectivities of the hydrogenation of compounds (Ia), (III), and (V) are typically higher in acetone than in MeOH and comparable to those obtained with other more enantioselective ruthenium-BINAP type catalysts. The asymmetric reduction of ketones results in only poor enantioselectivities.