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Synfacts 2015; 11(1): 0065
DOI: 10.1055/s-0034-1379689
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Axially Chiral Biaryl Compounds via Dynamic Kinetic Resolution

Contributor(s):
Mark Lautens
,
Zafar Qureshi
Hazra CK, Dherbassy Q, Wencel-Delord J, * Colobert F. * Université de Strasbourg, France
Synthesis of Axially Chiral Biaryls through Sulfoxide-Directed Asymmetric Mild C–H Activation and Dynamic Kinetic Resolution.

Angew. Chem. Int. Ed. 2014;
53: 13871-13875
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

palladium - chiral sulfoxides - atropisomers

Significance

Axially chiral biaryl motifs are privileged structures as ligands for transition-metal catalysis. The authors present a dynamic kinetic resolution of racemic biaryls with a palladium catalyst using point chirality of a sulfoxide directing group.


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Comment

Although some substrates were slow to react (up to 7 days), good yields and stereoselectivities were observed. Treatment of the products with t-BuLi at –90 °C led to an axially stable aryllithium species, which was trapped with CO2.


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