Premium
Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
Author(s) -
Jones Benjamin A.,
Balan Tudor,
Jolliffe John D.,
Campbell Craig D.,
Smith Martin D.
Publication year - 2019
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.201814381
Subject(s) - kinetic resolution , counterion , enantioselective synthesis , scalability , catalysis , kinetic energy , combinatorial chemistry , ammonium , resolution (logic) , chemistry , range (aeronautics) , salt (chemistry) , computational chemistry , organic chemistry , computer science , materials science , ion , physics , quantum mechanics , database , artificial intelligence , composite material
BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C 2 ‐ and non‐ C 2 ‐symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom