Synthesis of Homoallylic Alcohols with Acyclic Quaternary Centers through CoIII‐Catalyzed Three‐Component C−H Bond Addition to Internally Substituted Dienes and Carbonyls

作者: Sun Dongbang , Zican Shen , Jonathan A. Ellman

DOI: 10.1002/ANIE.201906633

关键词: CatalysisIsopreneChemistryCobaltStereocenterC h bondHomogeneous catalysisMedicinal chemistrySubstrate (chemistry)Component (thermodynamics)

摘要: An efficient CoIII -catalyzed three-component strategy to prepare homoallylic alcohols containing acyclic quaternary centers is disclosed. This transformation enables the introduction of two C-C σ bonds through C-H bond activation and sequential addition internally substituted dienes a wide range aldehydes activated ketones. Isoprene other monosubstituted are effective inputs, with reaction proceeding high diastereoselectivity for those substrate combinations that result in more than one stereogenic center. Moreover, opposite relative stereochemistry can be achieved by employing 1,2-disubstituted dienes. A mechanism proposed based upon products studies isotopically labeled starting materials.

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