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Enantioselective Copper-Catalyzed Arylation-Driven Semipinacol Rearrangement of Tertiary Allylic Alcohols with Diaryliodonium Salts

Author:
Lukamto, Daniel H., Gaunt, Matthew J.
Source:
Journal of the American Chemical Society 2017 v.139 no.27 pp. 9160-9163
ISSN:
1520-5126
Subject:
Lewis acids, alcohols, arylation, catalysts, copper, enantioselectivity, ketones, salts
Abstract:
A copper-catalyzed enantioselective arylative semipinacol rearrangement of allylic alcohols using diaryliodonium salts is reported. Chiral Cu(II)-bisoxazoline catalysts initiate an electrophilic alkene arylation, triggering a 1,2-alkyl migration to afford a range of nonracemic spirocyclic ketones with high yields, diastereo- and enantioselectivities.
Agid:
6031193