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Synfacts 2010(11): 1257-1257  
DOI: 10.1055/s-0030-1258796
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tetrasubstituted Alkenes through a Stannyllithiation

Contributor(s): Mark Lautens, Jane Panteleev
H. Tsuji*, Y. Ueda, L. Ilies, E. Nakamura*
The University of Tokyo, Japan
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The authors disclose a stannyllithiation of diarylacetylenes to yield tetrasubstituted alkenes. Relatively few methods exist to access these synthons since regio- and stereoselectivity are often a problem. The utility of this strategy is showcased by a synthesis of two isomers of ­hydroxytamoxifen (5 and 6) and dibenzo[g,p]-chrysene (7).

Review: I. Beletskaya, C. Moberg Chem. Rev. 2006, 106, 2320-2354.