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Peer-reviewedCC BY 4.0Organic Letters

Enantioselective Benzylic C–H Insertions with Diazosuccinate Esters

  • Nicholas M. Kamuti1
  • Bijaya Bagale1
  • Scott D. Bunge1
  • Albert J. Ndakala2
  • Jeffrey D. Mighion1
  1. 1Department of Chemistry and Biochemistry, College of Arts and Sciences, Kent State University, Kent, Ohio 44242, United States
  2. 2Department of Chemistry, Faculty of Science and Technology, University of Nairobi, Nairobi 00100, Kenya
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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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Cite

BibTeXRIS
BibTeX
@article{kamuti2026enantioselective,
  title = {{Enantioselective Benzylic C–H Insertions with Diazosuccinate Esters}},
  author = {Nicholas M. Kamuti and Bijaya Bagale and Scott D. Bunge and Albert J. Ndakala and Jeffrey D. Mighion},
  journal = {Organic Letters},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.orglett.6c03819},
  url = {https://doi.org/10.1021/acs.orglett.6c03819},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Enantioselective Benzylic C–H Insertions with Diazosuccinate Esters
AU  - Nicholas M. Kamuti
AU  - Bijaya Bagale
AU  - Scott D. Bunge
AU  - Albert J. Ndakala
AU  - Jeffrey D. Mighion
PY  - 2026
DA  - 2026/10/09
JO  - Organic Letters
DO  - 10.1021/acs.orglett.6c03819
UR  - https://doi.org/10.1021/acs.orglett.6c03819
AB  - 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.
SN  - 1523-7060
SN  - 1523-7052
ER  -