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Synfacts 2015; 11(1): 0044
DOI: 10.1055/s-0034-1379694
DOI: 10.1055/s-0034-1379694
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls
Further Information
Publication History
Publication Date:
15 December 2014 (online)
Significance
Several bioactive molecules contain an axially chiral biaryl subunit. Although several methods exist for their synthesis, the use of direct C–H functionalization is less well studied. The authors present a rhodium-catalyzed dehydrogenative Heck coupling to produce axially chiral biaryls using the Cramer complex.
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Comment
The substrate scope showed variability in the aza biaryl starting material and the olefin coupling partner. The products were shown to be competent in rhodium-catalyzed 1,4-additions to cyclohexenone with phenylboronic acid, producing the adduct in up to 77% yield and with 68% ee.
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