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Synfacts 2011(5): 0547-0547  
DOI: 10.1055/s-0030-1259780
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes

Contributor(s): Paul Knochel, Andreas J. Wagner
A. M. DeBerardinis, M. Turlington, L. Pu*
University of Virginia, Charlottesville, USA
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

The authors report a highly enantio­selective organocatalyst based on octahydro-BINOL for the reaction of various vinyl iodides with a range of aliphatic and aromatic aldehydes via an iodine-zinc exchange using diethylzinc. Substituted and functionalized allylic alcohols can be obtained in high enantiomeric purity under mild reaction conditions.