Download PDF
Synfacts 2008(3): 0290-0290  
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

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
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)

    Permissions and Reprints

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.