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Enantioselective Intramolecular Nicholas Reaction Catalyzed by Chiral Phosphoric Acid: Enantioconvergent Synthesis of Seven‐Membered Cyclic Ethers from Racemic Diols
Author(s) -
Ota Yusuke,
Kondoh Azusa,
Terada Masahiro
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.201808239
Subject(s) - enantioselective synthesis , chemistry , moiety , intramolecular force , phosphoric acid , organic chemistry , enantiomer , catalysis , derivatization , high performance liquid chromatography
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.