Synthesis 2016; 48(06): 816-827
DOI: 10.1055/s-0035-1561313
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© Georg Thieme Verlag Stuttgart · New York

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

Thorsten H. Wöste
a  Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
,
Kilian Muñiz*
a  Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
b  Catalan Institution for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona, Spain   Email: kmuniz@iciq.es
› Author Affiliations
Further Information

Publication History

Received: 17 November 2015

Accepted after revision: 14 December 2015

Publication Date:
13 January 2016 (online)

Abstract

A procedure for the intermolecular enantioselective dioxygenation of alkenes under iodine(III) catalysis has been developed. This protocol employs Selectfluor as the terminal oxidant together with a defined C 2-symmetric aryl iodide as the organocatalyst. This enantioselective reaction proceeds under mild conditions and converts a series of terminal and internal styrenes into the corresponding vicinal diacetoxylation products with up to 96% ee.

Supporting Information

 
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