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Synfacts 2010(4): 0434-0434  
DOI: 10.1055/s-0029-1219480
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Conjugate Addition of Acetylene Nucleophiles

Contributor(s): Mark Lautens, Stephen G. Newman
O. V. Larionov, E. J. Corey*
Harvard University, Cambridge, USA
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Publikationsdatum:
22. März 2010 (online)

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Significance

The enantioselective metal-catalyzed conjugate addition of sp² nucleophiles is a well-established transformation. In contrast, the addition of sp nucleophiles (i.e. acetylides) has proven much more challenging. Expanding on previous work (Y.-S. Kwak, E. J. Corey Org. Lett. 2004, 6, 3385), the authors have identified a nickel(II) catalyst system which, in the presence of a novel BINAP-type phosphine ligand, allows conjugate addition of aluminum acetylides in good yields and enantioselectivities.