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Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers
A highly regio‐ and diastereoselective nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl ketones and cyclopropyl carbinol derivatives using TMSBr, DMPSCl and TMSN(3) as nucleophiles has been developed. A variety of acyclic tertiary alkyl bromides, chlorides and azides we...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9324837/ https://www.ncbi.nlm.nih.gov/pubmed/35471589 http://dx.doi.org/10.1002/anie.202203673 |
Sumario: | A highly regio‐ and diastereoselective nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl ketones and cyclopropyl carbinol derivatives using TMSBr, DMPSCl and TMSN(3) as nucleophiles has been developed. A variety of acyclic tertiary alkyl bromides, chlorides and azides were therefore prepared with excellent diastereopurity. The substitution occurs at the most substituted quaternary carbon center in a stereoinvertive manner, which may be attributed to the existence of a bicyclobutonium species. |
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