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Synthesis of Spirocyclic Ethers by Enantioselective Copper‐Catalyzed Carboetherification of Alkenols
Author(s) -
Karyakarte Shuklendu D.,
Um Chanchamnan,
Berhane Ilyas A.,
Chemler Sherry R.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201808554
Subject(s) - enantioselective synthesis , copper , catalysis , chemistry , organic chemistry , stereochemistry
Abstract Spirocyclic ethers can be found in bioactive compounds. This copper‐catalyzed enantioselective alkene carboetherification provides 5,5‐, 5,6‐ and 6,6‐spirocyclic products containing fully substituted chiral carbon centers with up to 99 % enantiomeric excess. This reaction features the formation of two rings from acyclic substrates, 1,1‐disubstituted alkenols functionalized with either arenes, alkenes, or alkynes, and clearly constitutes a powerful way to synthesize chiral spirocyclic ethers.