Open AccessCopper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers
Author(s) -
Ilyas A. Berhane,
Ameya S. Burde,
Jonathan J. Kennedy-Ellis,
Eva Zurek,
Sherry R. Chemler
Publication year - 2021
Publication title -
chemical communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.837
H-Index - 333
eISSN - 1364-548X
pISSN - 1359-7345
DOI - 10.1039/d1cc03515k
Subject(s) - enantioselective synthesis , alkene , catalysis , ligand (biochemistry) , chemistry , copper , solvent , formal synthesis , organic chemistry , combinatorial chemistry , medicinal chemistry , receptor , biochemistry
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.