Journal of the American Chemical Society

Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings

SL Zultanski, GC Fu

Index: Zultanski, Susan L.; Fu, Gregory C. Journal of the American Chemical Society, 2011 , vol. 133, # 39 p. 15362 - 15364

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Citation Number: 91

Abstract

With the aid of a chiral nickel catalyst, enantioselective γ-(and δ-) alkylations of carbonyl compounds can be achieved through the coupling of γ-haloamides with alkylboranes. In addition to primary alkyl nucleophiles, for the first time for an asymmetric cross-coupling of an unactivated alkyl electrophile, an arylmetal, a boronate ester, and a secondary (cyclopropyl) alkylmetal compound are shown to couple with significant enantioselectivity. ...