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Direct Carbon-Carbon Bond Formation via Soft Enolization: A Facile and Efficient Synthesis of 1,3-Diketones

Daniel Lim, Fang Fang, Guoqiang Zhou and Don M. Coltart*

*Department of Chemistry, Duke University, Durham, North Carolina 27708, Email: don.coltartduke.edu

D. Lim, F. Fang, G. Zhou, D. M. Coltart, Org. Lett., 2007, 9, 4139-4142.

DOI: 10.1021/ol701599v (free Supporting Information)


Abstract

Ketones undergo soft enolate formation and acylation on treatment with MgBr2ˇOEt2, i-Pr2NEt, and various acylating agents to give 1,3-diketones. A particularly simple and efficient acylation with N-acylbenzotriazoles and O-Pfp esters can be conducted in untreated, reagent-grade CH2Cl2 open to the air.

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Direct Carbon-Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002

G. Zhou, D. Lim, D. M. Coltart, Org. Lett., 2008, 10, 3809-3812.


Key Words

1,3-Diketones


ID: J54-Y2007-3170