Synthesis of Bicyclic Salicylates by [3+3] Cyclization of 1,3-Bis(Silyl Enol Ethers) with Cyclic 3-(Silyloxy)alk-2-en-1-ones
| Autor: | Peter Langer, Nicole Höttecke, Christine Fischer, Helmut Reinke |
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| Rok vydání: | 2009 |
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| Zdroj: | Zeitschrift für Naturforschung B. 64:699-706 |
| ISSN: | 1865-7117 0932-0776 |
| Popis: | 1,3-Bis(silyl enol ethers) represent versatile synthetic building blocks [1]. In 1980, Chan and coworkers developed an elegant approach to salicylates based on formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 3-(silyloxy)alk-2-en-1-ones [2]. These cyclizations proceed by conjugated addition of the terminal carbon atom of the 1,3-bis(silyl enol ether) onto the 3-(silyloxy)alk-2-en-1-one and subsequent cyclization by intramolecular Mukaiyama aldol reaction. In recent years, we have reported the application of this method to the synthesis of a variety of functionalized arenes [3]. In their early work, Chan and coworkers also reported the synthesis of 5,6,7,8-tetrahydronaphthalenes by cyclization of 1,3bis(silyl enol ethers) with 3-(silyloxy)alk-2-en-1-ones prepared from cyclohexanone and tetralone. Herein, we report a systematic study of the [3+3] cyclization of 1,3-bis(silyl enol ethers) with various cyclic 3(silyloxy)alk-2-en-1-ones. |
| Databáze: | OpenAIRE |
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