Download PDF
Synlett 1998; 1998(4): 413-415
DOI: 10.1055/s-1998-1668
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Highly Regioselective Alkylation at the More Hindered γ-Site of Unsymmetrical Ketones by Use of Their Potassium Enolates. A Comparative Study with Lithium Enolates

Yannick Quesnel* , Laure Bidois-Sery, Jean-Marie Poirier, Lucette Duhamel
  • *Université de Rouen, UPRES-A 6014, IRCOF, F-76821 Mont Saint Aignan, Cedex, France; Fax 02 35 52 24 11; E-mail: Lucette.Duhamel@univ-rouen.fr
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Alkylation of regioisomeric potassium enolates 4 and 6 obtained from corresponding silyl enol ethers 2 and 3 occurs at the most substituted site affording ketones 8. Alkylation of corresponding lithium enolates 5 and 7 occurs at the expected site affording ketones 8 or 9. As an application the one pot synthesis of spiroketones 13 from silyl enol ethers 12 is described.

regioselectivity - alkylation - potassium enolates - lithium enolates

      >