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Synthesis 2017; 49(13): 2901-2906
DOI: 10.1055/s-0036-1588808
DOI: 10.1055/s-0036-1588808
special topic
Enantioselective 4-Hydroxylation of Phenols under Chiral Organoiodine(I/III) Catalysis
Weitere Informationen
Publikationsverlauf
Received: 01. März 2017
Accepted after revision: 05. April 2017
Publikationsdatum:
04. Mai 2017 (online)
Published as part of the Special Topic Modern Strategies with Iodine in Synthesis
Abstract
A procedure for the intermolecular enantioselective dearomatization of phenols under chiral (I/III) catalysis is reported. This protocol employs 3-chloroperoxybenzoic acid (m-CPBA) as the terminal oxidant together with a defined C 2-symmetric aryl iodide as the effective organocatalyst. This enantioselective reaction proceeds with complete selectivity under mild conditions and enables the hydroxylative dearomatization of a number of phenols to give the corresponding p-quinol products with up to 50% ee.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588808.
- Supporting Information
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For reviews on enantioselective iodine(III) catalysis:
For application of the corresponding amination–dearomatization, see:
For related contributions: