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Chiral 1,1′‐Binaphthyl‐2,2′‐Disulfonic Acid (BINSA) and Its Derivatives for Asymmetric Catalysis
Author(s) -
Hatano Manabu,
Ishihara Kazuaki
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300256
Subject(s) - organocatalysis , chemistry , brønsted–lowry acid–base theory , enantioselective synthesis , catalysis , phosphoric acid , organic chemistry , acid catalysis , combinatorial chemistry
Chiral Brønsted acid catalysts, which are derived from commercially available ( R )‐ or ( S )‐ 1,1′‐bi‐2‐naphthol (BINOL), have found widespread application as chiral organocatalysts and chiral ligands for metal species. The Brønsted acidity of these catalysts is considered to be associated with their catalytic activity. Therefore, due to the rapid development of asymmetric organocatalysis, chiral 1,1′‐binaphthyl‐2,2′‐disulfonic acid (BINSA) and the corresponding chiral binaphthyl disulfonimides are highly attractive as stronger chiral Brønsted acid catalysts than carboxylic acids, phosphoric acids, and phosphoramides. This Focus Review summarizes the latest achievements in chiral BINSA chemistry, particularly in the field of asymmetric organocatalysis.