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Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.

ABSTRACT: The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ₁ receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

SUBMITTER: Berhane IA

PROVIDER: S-EPMC8590114 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.

Berhane Ilyas A IA Burde Ameya S AS Kennedy-Ellis Jonathan J JJ Zurek Eva E Chemler Sherry R SR

Chemical communications (Cambridge, England) 20210930 78

The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ<sub>1</sub> receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented. ...[more]

PMID: 34518847

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