Palladium??Catalyzed Asymmetric Quaternary Stereocenter Formation

AL Gottumukkala, K Matcha, M Lutz…

Index: Gottumukkala, Aditya L.; Matcha, Kiran; Lutz, Martin; De Vries, Johannes G.; Minnaard, Adriaan J. Chemistry - A European Journal, 2012 , vol. 18, # 22 p. 6907 - 6914

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Citation Number: 31

Abstract

Abstract An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β, β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl 2, PhBOX, and AgSbF 6, and provides products in up to 99% enantiomeric excess, with good yields. Based on this strategy,(−)-α-cuparenone has been prepared in only two steps.