Facile synthesis of amino acid-derived novel chiral hypervalent iodine(V) reagents and their applications

Amino acid-derived novel chiral hypervalent iodine(V) reagents were synthesized from the corresponding chiral iodoarenes through DMDO oxidations. Their oxidation states were determined by the C-13 NMR chemical shifts of the ipso-carbon of the iodine atom, HRMS analysis, and elemental analyses. They were applied to the enantioselective hydroxylative dearomatization/[4+2]-dimerization cascade reactions of phenol derivatives to afford the desired products with up to 58% ee. (C) 2016 Elsevier Ltd. All rights reserved.