An efficient partial reduction of α,β-unsaturated esters using DIBAL-H in flow

Masahito Yoshida, Hiroyuki Otaka, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The partial reduction of α,β-unsaturated esters and benzoate derivatives to form the corresponding aldehydes was achieved using a flow reactor system within 1 s at a high flow rate (18 mL min-1) under cryogenic conditions (-97°C). Commercially available diisobutylaluminium hydride (DIBAL-H) was used as the reductant. The desired enals and benzaldehyde derivatives, except for 4-methoxycinnamate and 4-methoxybenzoate, were formed selectively and redox economically in moderate to high yields.

Original languageEnglish
Pages (from-to)6010-6016
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number27
DOIs
Publication statusPublished - 2014 Sep

Keywords

  • Aldehydes
  • Chemoselectivity
  • Esters
  • Flow synthesis
  • Reduction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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