Allylic alkylation. Palladium-catalyzed substitutions of allylic carboxylates. Stereo-and regiochemistry

BM Trost, TR Verhoeven

Index: Trost,B.M.; Verhoeven,T.R. Journal of the American Chemical Society, 1980 , vol. 102, p. 4730

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Citation Number: 350

Abstract

Abstract: The reaction of allyl acetates with the sodium salt of dimethyl malonate or methyl benzenesulfonylacetate in the presence of catalytic quantities of tetrakis (tripheny1phosphine) palladium is probed. The reactivity of 1-(1'-acetoxyethy1) cycloalkenes falls in the order 5 k 7>> 6. The ability to invert the normal reactivity of two leaving groups is illustrated. With a trisubstituted double bond olefin stereochemistry is completely retained, ...

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