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Synfacts 2007(3): 0295-0295  
DOI: 10.1055/s-2007-968277
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu(II)-Desymmetrization of meso-1,2-Diols with C 2-Symmetric Chiral Piperazines

Contributor(s): Mark Lautens, Frédéric Ménard
D. Nakamura, K. Kakiuchi, K. Koga, R. Shirai*
Nara Institute of Science and Technology and Doshisha Women’s College of Liberal Arts, Kyoto, Japan
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Chemical alternatives to enzymatic desymmetrization by acylation of meso-diols have been a subject of tremendous interest. The new class of chiral diamines (5 and 6) was shown to be efficient and to furnish desymmetrized diols with high enantioselectivity. The enantiopure ligand 6 was prepared on multigram scale in four steps from l-proline.