On the nucleophilic nature of a TMM-PdL2 intermediate: a direct palladium catalyzed addition of trimethylenemethane to heteroatom unsaturation

BM Trost, PJ Bonk

Index: Trost, Barry M.; Bonk, Peter J. Journal of the American Chemical Society, 1985 , vol. 107, # 26 p. 8277 - 8279

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Citation Number: 33

Abstract

(€ 3 summarize the results. Remarkably, reaction proceeds at or near room temperature (entries 1-3, 6, 9) although normally we found it convenient and more general to use refluxing dioxane. The chemoselectivity is excellent. Most surprising is the lack of cycloaddition to the double bond of a, P-unsaturated aldehydes (entries 4 and 5). The steroid (entry 9) shows the compatibility of other carbonyl functionalities. Apparently, our ...