Synthesis 2008(13): 2148-2152  
DOI: 10.1055/s-2008-1042947
PSP
© Georg Thieme Verlag Stuttgart · New York

MgBr2·OEt2-Promoted Coupling of Ketones and Activated Acyl Donors via Soft Enolization: A Practical Synthesis of 1,3-Diketones

Daniel Lim, Guoqiang Zhou, Alexandra E. Livanos, Fang Fang, Don M. Coltart*
Department of Chemistry, Duke University, Durham, NC 27708, USA
Fax: +1(919)6601605; e-Mail: don.coltart@duke.edu;
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Publikationsverlauf

Received 2 November 2007
Publikationsdatum:
18. März 2008 (online)

Abstract

Ketones undergo soft enolization and acylation on treatment with MgBr2·OEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-pentafluorophenyl esters, and, in these cases, is conducted using untreated, reagent grade CH2Cl2 open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.