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, vol.61, no.34, pp.8212-8217, 2005 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 61 Issue: 34
  • Publication Date: 2005
  • Doi Number: 10.1016/j.tet.2005.06.031
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.8212-8217


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.