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Synlett 2001; 2001(9): 1403-1406
DOI: 10.1055/s-2001-16808
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A Novel Protocol for Construction of Indolylmethyl Group at Aldehydes or Ketones

Hidetoshi Tokuyama* , Manabu Watanabe, Yuki Hayashi, Toshiki Kurokawa, Ge Peng, Tohru Fukuyama
  • *Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, The Japan Science and Technology Corporation (JST), 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan; Fax + 81(3)58 02 86 94; E-mail: fukuyama@mol.f.u-tokyo.ac.jp
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Publication Date:
28 August 2001 (online)

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A new method for introduction of indolylmethyl group to aldehydes or ketones using diethyl (o-isocyanophenylmethyl)phosphonate through Horner-Wadsworth-Emmons condensation, thiol-mediated radical cyclization, and the subsequent desulfurization is described. The Horner-Wadsworth-Emmons reagent was prepared from 2-nitrobenzaldehyde in a concise three-step sequence.

3-substituted indoles - diethyl (o-isocyanophenylmethyl)phosphonate - Horner-Wadsworth-Emmons condensation - 2-alkenylphenylisocyanides - thiol-mediated radical cyclization

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