The Journal of Organic Chemistry

Organotin nucleophiles. 5. Palladium-catalyzed allylic propargylation with allenylstannane

E Keinan, M Peretz

Index: Keinan, Ehud; Peretz, Moshe Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5302 - 5309

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Citation Number: 66

Abstract

Allenyltrialkylstannanes were found to react with various allylic acetates in the presence of catalytic amounts of Pd (PPhd4 under mild neutral conditions, providing a novel approach for obtaining the 1, 5-enyne carbon skeleton. The regioselectivity of propargylation depends largely on the electron-withdrawing properties of the substituents at the two ends of the allylic system: substitution occurs at the end of closer proximity to the more electronegative ...