Premium
Development of Chiral Sulfoxide Ligands for Asymmetric Catalysis
Author(s) -
Trost Barry M.,
Rao Meera
Publication year - 2015
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.201411073
Subject(s) - enantiopure drug , sulfoxide , chirality (physics) , combinatorial chemistry , enantioselective synthesis , ligand (biochemistry) , chemistry , catalysis , chiral ligand , stereochemistry , organic chemistry , chiral anomaly , physics , biochemistry , receptor , fermion , quantum mechanics , nambu–jona lasinio model
Nitrogen‐, phosphorus‐, and oxygen‐based ligands with chiral backbones have been the historic workhorses of asymmetric transition‐metal‐catalyzed reactions. On the contrary, sulfoxides containing chirality at the sulfur atom have mainly been used as chiral auxiliaries for diastereoselective reactions. Despite several distinct advantages over traditional ligand scaffolds, such as the proximity of the chiral information to the metal center and the ability to switch between S and O coordination, these compounds have only recently emerged as a versatile class of chiral ligands. In this Review, we detail the history of the development of chiral sulfoxide ligands for asymmetric catalysis. We also provide brief descriptions of metal–sulfoxide bonding and strategies for the synthesis of enantiopure sulfoxides. Finally, insights into the future development of this underutilized ligand class are discussed.