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Synfacts 2011(7): 0751-0751  
DOI: 10.1055/s-0030-1260649
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of syn- and anti-1,2-Hydroxyalkyls

Contributor(s): Mark Lautens, Patrick T. Franke
M. Fañanás-Mastral, B. ter Horst, A. J. Minnaard, B. L. Feringa*
University of Groningen, The Netherlands
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Feringa and co-workers developed a stereoselective synthesis affording syn- and ­anti-1,2-hydroxyalkyl structures via a copper-­catalyzed asymmetric allylic alkylation of δ-alkoxy-substituted allylic bromides with Grignard reagents. Depending on which enantiomer of the ligand is employed, a matched or mismatched situation is present affording highly valuable compounds with complete regiocontrol and excellent stereocontrol.