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Gearing
between the a-carbon atom and
the nitrogen atom of an amino acid relays chiral information to the Pd(II)
center which cleaves C-H bonds asymmetrically. In this communication we report
on the first example of Pd(II)-catalyzed enantioselective alkylation of sp2
and sp3 C-H bonds with boronic acids.
Angew. Chem. Int. Ed., 2008, Selected as Hot Paper and for front cover, 47, 4761.
O-Methyl
hydroxamic acids, as carboxylic acid derivatives, undergo b-C-H cleavages by Pd(II) catalysts and
subsequent coupling with boronic acids to form carbon-carbon bonds. Air is used
as the oxidant.
J. Am. Chem. Soc., 2008,
130, 7190.
Characterization of this trinuclear C-H activation intermediate provides
insights into the origin of the reactivity and stereoselectivity of Pd(II)
insertion into the inert C-H bonds
Angew. Chem. Int. Ed., 2005, 44, 2122.
