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Synfacts 2006(1): 0038-0038  
DOI: 10.1055/s-2005-921672
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Allylic Alcohols via [3,3]-Sigmatropic Rearrangement

Contributor(s): Mark Lautens, Andrew Martins
E. E. Lee, R. A. Batey*
University of Toronto, Canada
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

Using a COP-Cl/AgOTFA catalyst system, (allyloxy)iminodiazaphospholidines can be converted into enantioenriched allylamines in an Overman-type rearrangement. E-Substituted substrates afford products of S configuration whereas Z-substituted substrates lead to R configuration in good to excellent yields and enantiomeric excesses.