Building Up Quarternary Stereocenters of Chromans by Asymmetric Redox Organocatalysis: A New Entry to Vitamin E

High‐turnover catalysis offers a novel concept for the efficient chemo‐ and enantioselective preparation of chroman intermediates, which are useful for the synthesis of tocopherols (vitamin E components) and other biologically active compounds. A chiral ammonium iodide catalyst mediates the cycloeth...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-12, Vol.53 (52), p.14313-14315
1. Verfasser: Netscher, Thomas
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description High‐turnover catalysis offers a novel concept for the efficient chemo‐ and enantioselective preparation of chroman intermediates, which are useful for the synthesis of tocopherols (vitamin E components) and other biologically active compounds. A chiral ammonium iodide catalyst mediates the cycloetherification in combination with a cooxidant and an inorganic base in excellent yield and up to 93 % ee. OTs=para‐toluenesulfonyl.
doi_str_mv 10.1002/anie.201409826
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subjects Ammonium Compounds
antioxidants
asymmetric catalysis
biological activity
Catalysis
Chromans - chemistry
Oxidation-Reduction
Quaternary Ammonium Compounds - chemistry
Stereoisomerism
tocopherols
tocotrienols
Tosyl Compounds - chemistry
Vitamin E - chemical synthesis
Vitamin E - chemistry
title Building Up Quarternary Stereocenters of Chromans by Asymmetric Redox Organocatalysis: A New Entry to Vitamin E
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