Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.
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Authors
Cahard, Elise
Male, Henry PJ
Tissot, Matthieu
Gaunt, Matthew J
Abstract
A catalytic enantioselective and regiodivergent arylation of alkenes is described. Chiral copper(II)bisoxazoline complexes catalyze the addition of diaryliodonium salts to allylic amides in excellent ee. Moreover, the arylation can be controlled by the electronic nature of the diaryliodonium salt enabling the preparation of nonracemic diaryloxazines or β,β'-diaryl enamides.
Description
Keywords
Allyl Compounds, Amides, Catalysis, Copper, Hydrocarbons, Aromatic, Onium Compounds, Oxazines, Oxazoles, Stereoisomerism
Journal Title
J Am Chem Soc
Conference Name
Journal ISSN
0002-7863
1520-5126
1520-5126
Volume Title
137
Publisher
American Chemical Society (ACS)
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/I00548X/1)
We are grateful to EPSRC, GSK and the University of Cambridge
(E.C., H.P.J.M. & M.T.) and the ERC and EPSRC for fellowships
(M.J.G.). Mass spectrometry data were acquired at the EPSRC UK
National Mass Spectrometry Facility at Swansea University.