Trimethylcyanosilane as a Convenient Reagent for the Preparation of Trimethylsilyl Enol Ethers of 1,3-Diketones 英文参考文献.docVIP

Molecules 1999, 4, 310-315 molecules ISSN 1420-3049 Trimethylcyanosilane as a Convenient Reagent for the Preparation of Trimethylsilyl Enol Ethers of 1,3-Diketones Jin-Cong Zhuo College of Pharmacy, The Ohio State University, Columbus, Ohio 43221, USA Tel.: (614)-688-3149, Fax: (614)-292-2435, E-mail: zhuo.1@ Received: 22 August 1999 / Accepted: 12 September 1999 / Published: 10 October 1999 Abstract: Trimethylsilyl enol ethers of 1,3-diketones are generated “in situ” or obtained in high isolated yield by the reaction of 1,3-diketones with trimethylcyanosilane in various solvents such as cyclohexane, hexane, benzene, methylene chloride, chloroform, carbon tet- rachloride, and acetonitrile. Keywords: Trimethylcyanosilane, Silylation, 1,3-Diketones, Trimethylsilyl enol ethers. Introduction Silyl enol ethers of 1,3-diketones are effective silylating agents and useful precursors for the prepa- ration of Diels-Alder dienes, 1,3-bis(silyloxy)buta-1,3-dienes. They have found extensive application in organic synthesis. The preparation of the silyl enol ethers of 1,3-diketones resulted in only fair yields by using reagents such as trimethylchlorosilane/strong bases [1], bis(trimethylsilyl)formamide [2], bis(trimethylsilyl)acetamide [3], triethylsilyl-thiobenzene [4], trimethylsilyl trifluoromethanesul- fonate [5], and ethyl trimethylsilylacetate/tetra-n-butylamonium fluoride [6], employed previously for the silylation of carbonyl compounds. A few methods for the preparation of trimethylsilyl enol ethers of 1,3-diketones have been developed by using hexamethyldisilazane [7], hexamethyl- disilazane/imidazole [8], 2-oxo-3-trimethylsilyltetrahydro-1,3-oxazole [9], and (trimethylsilyl)- diethylamine /methyl iodide [10]. ? 1999 by the authors. Reproduction of this article, by any means, is permitted for noncommercial purposes.  311 Molecules 1999, 4 Trimethylcyanosilane (Me3SiCN) has been u