Journal of the American Chemical Society 2004-04-14

Copper-catalyzed tandem conjugate addition-electrophilic trapping: ketones, esters, and nitriles as terminal electrophiles.

Kyriacos Agapiou, David F Cauble, Michael J Krische

Index: J. Am. Chem. Soc. 126 , 4528, (2004)

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Abstract

Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.