The Need for an Incisive Analysis of the Regioselectivity Associated with the Deprotonation of α-Alkoxy and α-Acyloxy Ketones

Leo A. Paquette; Steven V. O'Neil; Nathalie Guillo; Qingbei Zeng; David G. Young

doi:10.1055/s-1999-2959

Synlett 1999; 1999(12): 1857-1866
DOI: 10.1055/s-1999-2959

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The Need for an Incisive Analysis of the Regioselectivity Associated with the Deprotonation of α-Alkoxy and α-Acyloxy Ketones

Leo A. Paquette^* , Steven V. O'Neil, Nathalie Guillo, Qingbei Zeng, David G. Young

^*Evans Chemical Laboratories, The Ohio State University, Columbus, OH 43210, USA; Fax +1-6 14-2 92-16 85; E-mail: paquette.1@osu.edu

Abstract

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A summary of informative examples involving the regioselective deprotonation of α-oxygenated ketones has been compiled from the literature and augmented by new findings from the authors' laboratory. The text provides a brief discussion of the complexity of the matter. The data are tabulated with regard to enolization both away from and toward the oxygen substituent, with subsequent capture at oxygen or carbon. The possible role of steric, electronic, and conformational factors is addressed in a manner that points up the need for a more detailed understanding of these enolizations as a general process.

aldol reactions - alkylations - ethers - ketones - regioselectivity

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