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Synfacts 2010(11): 1257-1257
DOI: 10.1055/s-0030-1258796
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
H. Tsuji*, Y. Ueda, L. Ilies, E. Nakamura*
The University of Tokyo, Japan
Further Information
Publication History
Publication Date:
21 October 2010 (online)
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.