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Synfacts 2013; 9(3): 0283
DOI: 10.1055/s-0032-1318266
DOI: 10.1055/s-0032-1318266
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Ruthenium-Catalyzed Dynamic Kinetic Resolution of Cycloketones
Liu C, Xie J.-H, * Li Y.-L, Chen J.-Q, Zhou Q.-L. * Nankai University, Tianjin, P. R. of China
Asymmetric Hydrogenation of α,α′-Disubstituted Cycloketones through Dynamic Kinetic Resolution: An Efficient Construction of Chiral Diols with Three Contiguous Stereocenters.
Angew. Chem. Int. Ed. 2013;
52: 593-596
Asymmetric Hydrogenation of α,α′-Disubstituted Cycloketones through Dynamic Kinetic Resolution: An Efficient Construction of Chiral Diols with Three Contiguous Stereocenters.
Angew. Chem. Int. Ed. 2013;
52: 593-596
Further Information
Publication History
Publication Date:
15 February 2013 (online)
Significance
A ruthenium-catalyzed hydrogenation of racemic, diastereomeric α′-aryl cycloketones is reported. The reaction is a dynamic kinetic resolution (DKR) and gives chiral diols with three contiguous stereocenters with high yield and enantioselectivity.
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Comment
As the substrate consists of a mixture of four stereoisomers, exerting enantiocontrol in hydrogenation is a challenging feat. The DKR sets the α,α′-stereocenters and hydrogenates the ketone. When R1 is an ester, lactonization occurs and the lactone is hydrogenated to the diol. The α′-aryl substitutent is essential in the DKR. The synthetic utility of the DKR is demonstrated in the synthesis of (+)-γ-lycorane.
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