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Catalytic Asymmetric Synthesis of α‐Trifluoromethylated Carbinols: A Case Study of Tertiary Propargylic Alcohols
Author(s) -
Noda Hidetoshi,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2018
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.201800013
Subject(s) - stereocenter , chemistry , enantioselective synthesis , trifluoromethylation , combinatorial chemistry , catalysis , trifluoromethyl , organic chemistry , alkyl
Abstract Enantioenriched CF 3 ‐substituted tertiary alcohols have been applied in a broad range of chemical disciplines, including medicinal chemistry and agrochemistry. The widely prescribed anti‐HIV pharmaceutical efavirenz is one particular example of the application of these chiral building blocks. Because the typical synthetic route to this small drug molecule involves the stoichiometric use of a chiral promoter, significant effort has been devoted to the development of catalytic alternatives for accessing this building block. In this Focus Review, we summarize the catalytic asymmetric synthesis of CF 3 ‐substituted tertiary propargylic alcohols based on three retrosynthetic approaches, namely one trifluoromethylation approach and two building‐block strategies. The general challenges that are involved in the construction of a CF 3 ‐substituted tetrasubstituted stereogenic carbon species are highlighted and possible future directions in the field are discussed.