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Synfacts 2015; 11(1): 0044
DOI: 10.1055/s-0034-1379694
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Rhodium-Catalyzed Synthesis of Axially Chiral Biaryls

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Zheng J, You S.-L * Shanghai Institute of Organic Chemistry, P. R. of China
Construction of Axial Chirality by Rhodium-Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes.

Angew. Chem. Int. Ed. 2014;
53: 13244-13247
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

rhodium - biaryl ligands - axial chirality

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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