Download PDF
Synlett 1999; 1999(12): 1857-1866
DOI: 10.1055/s-1999-2959
account
© 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.

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
Further Information

Publication History

Publication Date:
31 December 1999 (online)

 PDF Download  Permissions and Reprints All articles of this category

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