Evans-Tishchenko Coupling of Heteroaryl Aldehydes

Philip D. Dorgan, Jamie Durrani, A. N. Hulme, Manuel Cases-Thomas

Research output: Contribution to journalArticlepeer-review

Abstract

The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with β-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 f 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.
Original languageEnglish
Pages (from-to)7475–7478
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number21
DOIs
Publication statusPublished - Nov 2010

Keywords

  • Evans-Tishchenko
  • beta-hydroxy ketone
  • anti-1,3 diol
  • samarium

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