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Synfacts 2009(12): 1369-1369  
DOI: 10.1055/s-0029-1218247
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Heteroaryl Titanates and Zinc Reagents in Enantioselective Conjugate Addition

Contributor(s): Mark Lautens, Chit Tsui
A. J. Smith, L. K. Abbott, S. F. Martin*
The University of Texas at Austin, USA
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Publikationsdatum:
20. November 2009 (online)

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Significance

The development of the enantioselective conjugate addition of aryl nucleophiles to Michael acceptors is an important objective in modern organic synthesis. The addition of 2-heteroaryl nucleophiles remains an obstacle mainly due to the instability of 2-heteroarylboronic acids. The authors describe a general strategy for the conjugate addition of 2-heteroaryl titanates and zinc reagents to cyclic enones, unsaturated lactones, and unsaturated lactams in high enantioselectivities and yields.