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Synfacts 2005(3): 0334-0334  
DOI: 10.1055/s-2005-921625
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Cross-Coupling of 1,1-Diborylalkenes

Contributor(s): Paul Knochel, Andrei Gavryushin
M. Shimizu*, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama
Kyoto University, Japan
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Publikationsdatum:
22. November 2005 (online)

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Significance

Triarylalkenes are an important class of antiestrogens, now widely used for cancer treatment. The stereocontrolled synthesis of this class of products is therefore of much interest. The Pd-catalyzed stepwise cross-coupling of gem-diborylalkenes and aryl iodides allows a stereoselective preparation of triarylalkenes. Important drugs like tamoxifen can be prepared in one pot by this method. gem-Diborylalkenes are sufficiently stable to be isolated and purified by usual chromatography.