[structure: see text] Full conversion and enantioselectivities up to 83% have been obtained in the conjugate addition reactions of diethyl zinc to Michael acceptors catalyzed by well-defined (chiral) copper(I) aminoarenethiolates. Interesting differences between organozinc or Grignard reagents have been found: for cyclic enones R(2)Zn reagents afford better results, whereas earlier work showed that RMgX reagents react more selectively with acyclic enones.
Enantioselective syntheses
Enantioselective syntheses O 0031Copper (I) Thiolate Catalysts in Asymmetric Conjugate Addition Reactions. -The addition of diethylzinc to a variety of Michael acceptors in the presence of catalytic amounts of salt-free copper(I) aminoarenethiolates (I)-(VI) is reported. Full conversion and enantioselectivities up to 83% are obtained. -(ARINK, A. M.; BRAAM, T. W.; KEERIS, R.; JASTRZEBSKI, J. T. B. H.; BENHAIM, C.; ROSSET, S.; ALEXAKIS*, A.; VAN KOTEN*, G.; Org. Lett. 6 (2004) 12, 1959-1962; Dep. Met. Mediated Synth., Debye Res. Inst., Utrecht Univ., NL-3584 CH Utrecht, Neth.; Eng.) -Steudel 39-030 2004 Enantioselective syntheses
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