Journal
TETRAHEDRON LETTERS
Volume 57, Issue 46, Pages 5103-5107Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.10.016
Keywords
Chiral hypervalent iodine(V) reagent; Asymmetric synthesis; Metal-free oxidation; Dearomatization; Dimerization
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Funding
- Research Promotion on SIS (the Society of Iodine Science)
- Grants-in-Aid for Scientific Research [16H04144] Funding Source: KAKEN
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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.
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