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A Copper(I)‐Catalyzed Enantioselective γ‐Boryl Substitution of Trifluoromethyl‐Substituted Alkenes: Synthesis of Enantioenriched γ,γ‐ gem ‐Difluoroallylboronates
Author(s) -
Kojima Ryoto,
Akiyama Sota,
Ito Hajime
Publication year - 2018
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.201803663
Subject(s) - enantioselective synthesis , stereospecificity , reagent , trifluoromethyl , chemistry , catalysis , substitution (logic) , copper , organic chemistry , optically active , substitution reaction , medicinal chemistry , combinatorial chemistry , alkyl , computer science , programming language
The first catalytic enantioselective γ‐boryl substitution of CF 3 ‐substituted alkenes is reported. A series of CF 3 ‐substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the corresponding optically active γ,γ‐ gem ‐difluoroallylboronates in high enantioselectivity. The thus obtained products could be readily converted into the corresponding difluoromethylene‐containing homoallylic alcohols using highly stereospecific allylation reactions.