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

Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt

doi:10.1021/jacs.5b03937

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

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

Authors

Elise Cahard¹, Henry P J Male¹, Matthieu Tissot¹, Matthew J Gaunt¹

Affiliation

¹ Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry*
Amides / chemistry*
Catalysis
Copper / chemistry*
Hydrocarbons, Aromatic / chemical synthesis
Hydrocarbons, Aromatic / chemistry*
Onium Compounds / chemistry*
Oxazines / chemical synthesis
Oxazines / chemistry
Oxazoles / chemistry*
Stereoisomerism

Substances

Allyl Compounds
Amides
Hydrocarbons, Aromatic
Onium Compounds
Oxazines
Oxazoles
Copper