Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes


Cinar M. E. , ENGELEN B., PANTHOEFER M., DEISEROTH H., SCHLIRF J., Schmittel M.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.12, pp.813-824, 2016 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 12
  • Publication Date: 2016
  • Doi Number: 10.3762/bjoc.12.80
  • Title of Journal : BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.813-824

Abstract

A one-pot transformation, which involves the reaction of ketones with aldehydes in the presence of metal halides to furnish tetrahydro-2H-pyran-2,4-diols in a highly diastereoselective manner, is investigated thoroughly by experiments and computations. The reaction was also successfully implemented on a flow micro reactor system.