A New and Practical Five-Carbon Component for Metal-Catalyzed [5 + 2] Cycloadditions: Preparative Scale Syntheses of Substituted Cycloheptenones
(Matrix Presented) Described herein is an efficient preparative scale synthesis of 1-(2-methyoxyethoxy)-1-vinylcyclopropane and the investigation of the utility of this reagent as a new five-carbon component in metal-catalyzed [5 + 2] cycloadditions. A new cycloaddition procedure is also described that proceeds up to 12-fold faster and with 10-fold less catalyst than previously described, providing cycloheptenones in many cases in minutes and in isolated yields of 75-97%. The procedure is readily conducted on a small or large scale (up to 100 mmol thus far).
Wender, Paul A.,Dyckman, Alaric J.,Husfeld, Craig O.,Scanio, Marc J. C.
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