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Synfacts 2010(4): 0442-0442  
DOI: 10.1055/s-0029-1219483
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Allylic Etherification Using a Novel COP Catalyst

Contributor(s): Mark Lautens, Stephen G. Newman
A. C. Olson, L. E. Overman*, H. F. Sneddon, J. W. Ziller
University of California, Irvine, USA
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Asymmetric allylic substitution ­reactions can provide rapid access to chiral allylic ethers. However, these reactions are often plagued by poor branched/linear ratios which need to be controlled through the appropriate choice of both substrate and catalyst. Extending on previous work with (Z)-allylic alcohols (Org. Lett. 2007, 9, 911), the authors present a highly enantioselective allylic substitution of (E)-2-alken-1-ols with phenols giving complete branched ­selectivity. Key to this new transformation was the development of a novel COP-type palladium catalyst.