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Synfacts 2010(8): 0933-0933  
DOI: 10.1055/s-0030-1257753
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoretentive Suzuki-Miyaura Coupling of Haloallenes

Contributor(s): Paul Knochel, Tobias Thaler
E. M. Woerly, A. H. Cherney, E. K. Davis, M. D. Burke*
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

A novel highly stereoselective method for the Suzuki-Miyaura coupling of halo­allenes was developed for the stereocontrolled construction of the norcartenoid (-)-peridinin. This straightforward total synthesis was performed by the iterative cross-coupling (ICC) of bifunctional haloboronic acids masked as N-methylimino­diacetic acid (MIDA) boronates.