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Synfacts 2011(4): 0351-0351  
DOI: 10.1055/s-0030-1259592
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of 1,1-Diarylethane Drugs

Contributor(s): Philip Kocienski
B. L. H. Taylor, E. C. Swift, J. D. Waetzig, E. R. Jarvo*
University of California, Irvine, USA
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Publikationsdatum:
18. März 2011 (online)

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Significance

Syntheses of the sleep-inducing H1-antihistamine K and the tubulin polymerization inhibitor N exemplify a general enantioselective synthesis of 1,1-diarylethanes using the stereo­specific nickel-catalyzed cross-coupling reactions of alkyl ethers with methylmagnesium iodide. Further seven examples are reported giving yields of 70-96% and ee values of 85-99%.