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High-turnover Hypoiodite Catalysis for Asymmetric Synthesis of Tocopherols

High-turnover Hypoiodite Catalysis for Asymmetric Synthesis of Tocopherols

Muhammet Uyanik, Hiroki Hayashi, Kazuaki Ishihara

Science. 2014 Jul 18;345(6194):291-4.

PMID: 25035486

Abstract:

The diverse biological activities of tocopherols and their analogs have inspired considerable interest in the development of routes for their efficient asymmetric synthesis. Here, we report that chiral ammonium hypoiodite salts catalyze highly chemo- and enantioselective oxidative cyclization of γ-(2-hydroxyphenyl)ketones to 2-acyl chromans bearing a quaternary stereocenter, which serve as productive synthetic intermediates for tocopherols. Raman spectroscopic analysis of a solution of tetrabutylammonium iodide and tert-butyl hydroperoxide revealed the in situ generation of the hypoiodite salt as an unstable catalytic active species and triiodide salt as a stable inert species. A high-performance catalytic oxidation system (turnover number of ~200) has been achieved through reversible equilibration between hypoiodite and triiodide in the presence of potassium carbonate base. We anticipate that these findings will open further prospects for the development of high-turnover redox organocatalysis.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13311450	Tetrabutylammonium triiodide		13311-45-0	Price

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