Journal of the American Chemical Society 2006-10-18

Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions.

Barry M Trost, James P Stambuli, Steven M Silverman, Ulrike Schwörer

Index: J. Am. Chem. Soc. 128 , 13328, (2006)

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Abstract

Transition-metal-catalyzed trimethylenemethane (TMM) [3 + 2] cycloadditions provide direct routes to functionalized cyclopentanes. This reaction has been shown to be a highly chemo-, regio-, and diastereoselective process. We report a palladium-catalyzed asymmetric [3 + 2] trimethylenemethane (TMM) cycloaddition between 3-acetoxy-2-trimethylsilylmethyl-1-propene and various di- and trisubstituted olefins. Yields of exo-methylenecyclopentane products range from 59 to 99%, and enantiomeric excesses range from 58 to 92% ee.