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Synlett 1998; 1998(4): 413-415
DOI: 10.1055/s-1998-1668
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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