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

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 1 receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, s...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (78), p.199-112
Main Authors: Berhane, Ilyas A, Burde, Ameya S, Kennedy-Ellis, Jonathan J, Zurek, Eva, Chemler, Sherry R
Format: Article
Language:English
Subjects:
Copper
Enantiomers
Ethers
Ligands
Styrenes
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Summary: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 1 receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented. The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc03515k