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. 2015 Jul 1;137(25):7986-9.
doi: 10.1021/jacs.5b03937. Epub 2015 Jun 19.

Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts

Elise Cahard  1 , Henry P J Male  1 , Matthieu Tissot  1 , Matthew J Gaunt  1
Affiliations

Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts

Elise Cahard et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1. Discovery of Regiodivergent Arylation
Scheme 2
Scheme 2. Electronically Controlled Regiodivergent Arylation
Scheme 3
Scheme 3. Application of β,β-diaryl enamides
See this image and copyright information in PMC

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