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Enantioselective Benzylic C-H Insertions with Diazosuccinate Esters
Nicholas M Kamuti1, Bijaya Bagale1, Scott D Bunge1
1Department of Chemistry and Biochemistry, College of Arts and Sciences, Kent State University, Kent, Ohio44242, United States.
Abstract:
The first enantioselective benzylic C-H insertion using α-alkyl-α-diazoesters, facilitated by a well-established chiral dirhodium(II) catalyst, is presented. This reaction selectively functionalizes primary benzylic C-H bonds with good to excellent enantioselectivity (up to 95% ee), thereby demonstrating the synthetic utility of this previously underexplored class of diazo reagents. The resulting differentiated diester products undergo selective monoester removal, thereby enabling subsequent functional-group manipulation of the liberated carboxylic acid and expanding access to enantioenriched building blocks.
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