4.4 Article

Synthesis of 3-(hydroxymethyl)-3-indol-3′-yloxindoles via Rh(II)-catalyzed three-component reaction of 3-diazooxindoles, indoles and formalin

Journal

TETRAHEDRON
Volume 71, Issue 22, Pages 3597-3602

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.02.053

Keywords

Mixed 3,3 '-bisindole; Carbene; Multi-component reaction; Zwitterion; Aldol addition

Funding

  1. NSF of China [21125209, 21332003, 21402051]
  2. MOST of China [2011CB808600]
  3. STCSM [12JC1403800]
  4. specialized Research Fund for The Doctoral Program of Higher Education [20130076120031]

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An efficient rhodium(II)-catalyzed three-component reaction of 3-diazooxindoles, indoles and formalin was reported. With this transformation, a series of 3-(hydroxymethyl)-3-indo1-3'-yloxindoles were easily afforded in good to excellent yields. The resulted 3-(hydroxymethyl)-3-indol-3'-yloxindole could be easily converted to the key intermediate for the total synthesis of gliocladin C. (C) 2015 Elsevier Ltd. All rights reserved.

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