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

Cinar M. E., Schmittel M.

MONATSHEFTE FUR CHEMIE, cilt.147, sa.11, ss.1925-1932, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 147 Sayı: 11
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1007/s00706-016-1841-4
  • Dergi Adı: MONATSHEFTE FUR CHEMIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1925-1932
  • İstanbul Teknik Üniversitesi Adresli: Hayır

Özet

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.