Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven‐Membered Cyclic Ethers from Racemic Diols

An enantioconvergent intramolecular Nicholas reaction of racemic diols was developed using BINOL‐ and SPINOL‐derived phosphoric acids as the chiral Brønsted acid catalyst. The developed reaction features an efficient approach to the synthesis of seven‐membered cyclic ethers in a highly enantioselect...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-10, Vol.57 (42), p.13917-13921
Main Authors: Ota, Yusuke, Kondoh, Azusa, Terada, Masahiro
Format: Article
Language:English
Subjects:
asymmetric catalysis
Brønsted acids
Chemical synthesis
cyclizations
Diols
Enantiomers
Ethers
organocatalysis
Phosphoric acid
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Summary:An enantioconvergent intramolecular Nicholas reaction of racemic diols was developed using BINOL‐ and SPINOL‐derived phosphoric acids as the chiral Brønsted acid catalyst. The developed reaction features an efficient approach to the synthesis of seven‐membered cyclic ethers in a highly enantioselective manner. Further derivatization of the enantioenriched cyclic ethers, initiated by the de‐complexation of the dicobalt species, afforded densely functionalized cyclic ethers having an unsaturated diester moiety without loss of enantiomeric excess. In the ‘nick' of time: An enantioconvergent intramolecular Nicholas reaction of racemic diols was developed using BINOL‐ and SPINOL‐derived phosphoric acids as the chiral Brønsted acid catalyst. The developed reaction features an efficient approach to the synthesis of seven‐membered cyclic ethers in a highly enantioselective manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201808239