Highly Regioselective Alkylation at the More-Hindered α-Site of Unsymmetrical Ketones by the Combined Use of Aluminum Tris (2, 6-diphenylphenoxide) and Lithium …

S Saito, M Ito, H Yamamoto

Index: Saito; Ito; Yamamoto Journal of the American Chemical Society, 1997 , vol. 119, # 3 p. 611 - 612

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Citation Number: 32

Abstract

An unsymmetrical dialkyl ketone can form two regioisomeric enolates upon deprotonation. 1 To exploit the synthetic potential of enolate ions, the regioselectivity of their formation must be controlled. By adjusting the conditions under which an enolate mixture is formed from a ketone, it is possible to establish either kinetic or thermodynamic control. Ideal conditions for kinetic control of the formation of less-substituted enolate are those in which deprotonation ...