Mn(III)-based C-C bond formation: regioselective alpha '-allylation of various alpha,beta-unsaturated, alpha and beta-alkoxy alpha,beta-unsaturated ketones

Tanyeli C., Ozdemirhan D.

TETRAHEDRON, cilt.61, sa.34, ss.8212-8217, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 34
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.tet.2005.06.031
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8212-8217
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

The Manganese(III) -based regioselective alpha'-keto radical generation of unsaturated ketones is a versatile synthetic procedure with broad applicability. The generated alpha'-keto radical slowly creates a metal enolate in a solvent at reflux. The resultant metal enolate affords the corresponding alpha'-allylated alpha,beta-unsaturated ketones in good yields. This method is the first example of the metal mediated regioselective alpha'-allylation of alpha,beta-unsaturated ketones. The ketones that have alpha or beta-alkoxy groups also work efficiently. (c) 2005 Elsevier Ltd. All rights reserved.