4.0 Article

Rh(I)-catalyzed asymmetric addition of arylboronic acids to NH isatins

Journal

TETRAHEDRON-ASYMMETRY
Volume 23, Issue 8, Pages 554-563

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2012.04.013

Keywords

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Funding

  1. NSFC [21072186, 20872139]
  2. West Light Foundation of CAS, Chengdu Institute of Biology of CAS [Y0B1051100]
  3. Major State Basic Research Development Program (973 program) [2010CB833300]

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The transition metal-catalyzed asymmetric variant of the title reaction is normally limited to N-protected isatins. However, Rh(I)/chiral sulfoxide phosphine complexes were found to catalyze the enantioselective addition of arylboronic acids to NH isatins under mild conditions. A variety of chiral 3-aryl-3-hydroxyl-2-oxindoles were obtained with high yields and with good to excellent enantioselectivities (85-92% ee). (C) 2012 Elsevier Ltd. All rights reserved.

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