4.5 Article

TMSOTf-Promoted Addition of Alkynes to Aldehydes: A Novel Synthesis of Chroman-4-ones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 32, Pages 5461-5469

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800782

Keywords

Addition; Aldehydes; Alkynes; Chromanone

Funding

  1. Korea Institute of Science and Technology (KIST) [2K01640, 2E20160]
  2. Ministry of Education, Science & Technology (MoST), Republic of Korea [2E20430, 2E20160] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. ( (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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