Highly stereoselective metal-mediated domino aldol reactions of propiophenone enolates with heteroaromatic, aliphatic, and unsaturated aldehydes


Cinar M. E. , Schmittel M.

MONATSHEFTE FUR CHEMIE, vol.147, no.11, pp.1925-1932, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 147 Issue: 11
  • Publication Date: 2016
  • Doi Number: 10.1007/s00706-016-1841-4
  • Journal Name: MONATSHEFTE FUR CHEMIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1925-1932
  • Istanbul Technical University Affiliated: No

Abstract

The one-pot reaction of propiophenone with heteroaromatic, aliphatic, and unsaturated aldehydes in the presence of metal halides furnishes racemic tetrahydro-2H-pyran-2,4-diols in a highly diastereo-selective manner. The mechanism for the stereoselective product formation as well as the surprising formation of a side product was explained on the basis of DFT computations.