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Domino asymmetric conjugate addition-conjugate addition.

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      Abstract

      Enantioenriched Al-, Mg-, and Zn-enolates undergo electrophilic trapping by nitroolefins and vinylsulfones to afford 1,4-diketones and 2-(bis(phenylsulfonyl)ethyl)ketones in good yield and excellent diastereoselectivity. A one-pot preparation of indenes and enantiopure syntheses of tetrahydrobenzofurans, tetrahydrobenzopyrroles, and azulenes are disclosed. A site-selective two-step sequence of three conjugate additions is also demonstrated.

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      Affiliations
      [1 ] Department of Organic Chemistry, University of Geneva , Quai Ernest Ansermet, 30, 1211 Geneva 4, Switzerland.
      Journal
      Org. Lett.
      Organic letters
      1523-7052
      1523-7052
      Apr 4 2014
      : 16
      : 7
      10.1021/ol5005752 24661026

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