Synfacts 2019; 15(06): 0619
DOI: 10.1055/s-0037-1611594
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric C–H Functionalization Using Chiral CpxCo(III) Catalysis

Contributor(s):
Mark Lautens
,
Egor M. Larin
Ozols K, Jang Y.-S, Cramer N. * École Polytechnique Fédérale de Lausanne, Switzerland
Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C–H Functionalizations.

J. Am. Chem. Soc. 2019;
141: 5675-5680
Further Information

Publication History

Publication Date:
20 May 2019 (online)

 

Significance

This work is an important advance in catalytic C–H functionalizations for the following reasons: (1) it is the first example of asymmetric C–H functionalization using a chiral Cpx-ligand-bound Co(III) complex; (2) it outperforms competing rhodium-catalyzed methods; (3) reactions with alkyl alkenes give regioisomeric products opposite to those with rhodium complexes.


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Comment

The authors systematically studied the effect of various substituents on the Cpx ligand in the C–H functionalization of chlorobenzamides, a benchmark for chiral CpRh(III) catalysis. The presence of the tert-butyl group greatly influences the approach of the olefin, whereas the naphthyl backbone acts to orient and align the metallocene.


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