Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation

Mio Shimogaki; Morifumi Fujita; Takashi Sugimura

doi:10.1002/anie.201609110

Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation

Angew Chem Int Ed Engl. 2016 Dec 19;55(51):15797-15801. doi: 10.1002/anie.201609110. Epub 2016 Nov 23.

Authors

Mio Shimogaki¹, Morifumi Fujita¹, Takashi Sugimura¹

Affiliation

¹ Graduate School of Material Science, University of Hyogo, 3-2-1 Kohto, Kamigori, Hyogo, Japan.

PMID: 27879045
DOI: 10.1002/anie.201609110

Abstract

The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.

Keywords: cyclization; enantioselectivity; heterocycles; hypervalent compounds; oxidation.

Publication types

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