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Building Up Quarternary Stereocenters of Chromans by Asymmetric Redox Organocatalysis: A New Entry to Vitamin E
Author(s) -
Netscher Thomas
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201409826
Subject(s) - stereocenter , enantioselective synthesis , organocatalysis , ammonium iodide , chemistry , catalysis , iodide , yield (engineering) , ammonium , organic chemistry , redox , combinatorial chemistry , materials science , metallurgy
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.