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Synfacts 2008(3): 0290-0290
DOI: 10.1055/s-2008-1042686
DOI: 10.1055/s-2008-1042686
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Lithiation of 2-Alkynyl Aryl Sulfides
R. Otte, B. Wibbeling, R. Fröhlich, S. Nakamura, N. Shibata, T. Toru*, D. Hoppe*
Westfälische Wilhelms-Universität Münster, Germany and Nagoya Institute of Technology, Japan
Further Information
Publication History
Publication Date:
21 February 2008 (online)
Significance
The Toru and Hoppe groups have collaborated to publish this interesting paper on asymmetric lithiation of 2-pyridinyl propargyl sulfides and their subsequent addition to aldehydes or protonation. These reactions proceed with good to moderate stereoselectivity. The alkynyl starting material is basically limited to the substrate indicated. The allenyl products were also shown to proceed in a Ni-catalyzed cross-coupling reaction. The stereochemical inversion associated with the lithium-to-titanium transmetallation is quite interesting.