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Synfacts 2011(4): 0404-0404  
DOI: 10.1055/s-0030-1259648
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrization of 2,2-Disubstituted
1,3-Propanediols

Contributor(s): Mark Lautens, Norman Nicolaus
J. Y. Lee, Y. S. You, S. H. Kang*
Korea Advanced Institute of Science and Technology, Daejeon, Korea
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

Using enantioselective desymmetrization protocols to prepare enantiomerically enriched molecules starting from symmetrical precursors is a very economic approach to generate chirality. However, the formation of quaternary ­stereogenic centers remains a challenging task. Herein, the authors present an asymmetric mono­benzylation of readily available 2,2-disubstituted 1,3-diols of type 1 using a catalyst formed from the chiral pyridinebisoxazoline (PyBox) ligand L* and CuCl2.