A simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts

VK Aggarwal*, Javier Vicente-Fidalgo, B Pelotier, IP Holmes, Roger V. Bonnert

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

27 Citations (Scopus)

Abstract

Aldehydes can be homologated to ketones in moderate to good yields using aryldiazomethanes generated in situ from tosylhydrazones. Chiral aldehydes can be employed with almost complete retention of configuration. The tosylhydrazones can also be generated in situ from the corresponding aldehyde leading to a one-pot process for coupling two different carbonyl compounds to give ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.

Translated title of the contributionA simple, user-friendly process for the homologation of aldehydes using tosylhydrazone salts
Original languageEnglish
Pages (from-to)10327-10331
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number52
Publication statusPublished - 23 Dec 2000

Keywords

  • ACID CATALYZED-REACTIONS
  • ETHYL DIAZOACETATE
  • AROMATIC-ALDEHYDES
  • TIN(II) CHLORIDE
  • ALPHA-ARYL
  • KETONES
  • ESTERS
  • CONVERSION

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