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Advances in Asymmetric Di‐and Trifluoromethylthiolation, and Di‐ and Trifluoromethoxylation Reactions
Author(s) -
Hardy Melissa A.,
Chachig Hélène,
Cahard Dominique
Publication year - 2019
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.201900004
Subject(s) - stereocenter , chemistry , heteroatom , moiety , fluorine , fluorocarbon , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , ring (chemistry) , catalysis
Methods to introduce fluorine atoms or fluoroalkyl groups are highly valuable to the design and development of biologically active compounds. To date, majority of fluorinated pharmaceuticals and agrochemicals bear a fluorine atom or CF 3 group at a non‐stereogenic center. The development of methods for the construction of new, emerging fluorinated motifs, in particular those combining a heteroatom and a fluorocarbon moiety have witnessed tremendous advancement in recent years; however, a challenging problem is the stereocontrol of a carbon center featuring such fluorinated motifs. This review aims to summarize the advancement in the asymmetric construction of trifluoromethylthio‐ and trifluoromethoxy compounds as well as their difluoromethyl analogues. Both the direct installation of the O−R f and S−R f groups (R f =CF 3 , CF 2 H) and the exploitation of building blocks featuring these groups are detailed.