Alcohol-Incorporating Diels-Alder Dimerization of In Situ Formed ortho-Quinamine via Co-Nitrenoid Insertion

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We disclose herein a Cp*Co(III)(LX)-catalyzed dearomative Diels-Alder dimerization of 2,6-disubstituted phenyl azidoformates. Upon the postulated cobalt-nitrenoid insertion into the neighboring ortho-carbon, the key intermediate of ortho-quinamine was generated for the subsequent dimeric cycloaddition process. A series of experimental and computational studies suggested that the quinolinol ligand of the cobalt catalyst plays a crucial role in the alcoholic solvent incorporation into the o-quinamine moiety, thereby enabling the Diels- Alder dimerization to furnish the bridged tricyclic bisamidation products.
Publisher
AMER CHEMICAL SOC
Issue Date
2022-08
Language
English
Article Type
Article
Citation

ORGANIC LETTERS, v.24, no.31, pp.5845 - 5850

ISSN
1523-7060
DOI
10.1021/acs.orglett.2c02392
URI
http://hdl.handle.net/10203/298640
Appears in Collection
CH-Journal Papers(저널논문)
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