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Synfacts 2010(5): 0549-0549  
DOI: 10.1055/s-0029-1219706
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Kinetic Resolution of Alcohols Through Si-O Coupling

Contributor(s): Mark Lautens, Jane Panteleev
A. Weickgenannt, M. Mewald, T. W. T. Muesmann, M. Oestreich*
Westfälische Wilhelms-Universität Münster, Germany
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Resolution of racemic alcohols through differential protection by a silyl group is a relatively new strategy. The Oestreich group devised a resolution through a diastereoselective dehydrogenative Si-O coupling using a chiral silane (Angew. Chem. Int. Ed. 2005, 44, 7620; see also: S. Rendler, M. Oestreich Angew. Chem. Int. Ed. 2008, 47, 248), which is distinctly different from the earlier reports of resolutions with TMSCl. This work outlines a development of a chiral catalyst to promote Si-O coupling of achiral silanes with alcohols bearing a chelating group.

Review: For a review on kinetic resolution, see: J. M. Keith, J. F. Larrow, E. N. Jacobsen Adv. Synth. Catal. 2001, 343, 5-26.