Synlett

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

Y Quesnel, L Bidois-Sery, JM Poirier, L Duhamel

Index: Quesnel, Yannick; Bidois-Sery, Laure; Poirier, Jean-Marie; Duhamel, Lucette Synlett, 1998 , # 4 p. 413 - 415

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Citation Number: 8

Abstract

Abstract: 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.

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