4.0 Article

Enantioselective α-tosyloxylation of ketones catalyzed by spirobiindane scaffold-based chiral iodoarenes

Journal

TETRAHEDRON-ASYMMETRY
Volume 22, Issue 23, Pages 2039-2055

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2011.12.003

Keywords

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Funding

  1. National Natural Science Foundation of China [20872064]
  2. Program for New Century Excellent Talents in University [NCET-07-0461]
  3. Tianjin Natural Science Foundation [09JCYBJC05900]
  4. Ministry of Education of China [B06005]

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Enantiomerically pure iodoarene (S)-2 and its derivatives (S)-3 to (S)-18 with a spirobiindane scaffold have been synthesized. The evaluation of these new chiral iodoarenes as catalysts in the enantioselective alpha-tosyloxylation of ketones was performed using m-CPBA as a stoichiometric oxidant, and the synthetically useful alpha-tosyloxylated ketones were obtained in up to 58% enantiomeric excess (ee). (C) 2011 Elsevier Ltd. All rights reserved.

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