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Synfacts 2010(8): 0897-0897  
DOI: 10.1055/s-0030-1257826
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of Axially Chiral Bis-sulfoxide Ligands

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
Q.-A. Chen, X. Dong, M.-W. Chen, D.-S. Wang, Y.-G. Zhou*, Y.-X. Li*
Dalian Institute of Chemical Physics, University of Science and Technology of China, Hefei and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Chiral auxiliaries containing sulfinyl groups have recently received considerable attention due to their optical stability, efficient transfer of chiral information, and accessibility in both enantiomeric forms. However, limited studies have been carried out on sulfoxide ligands of axial chirality. In this study the authors have successfully developed a highly diastereoselective synthetic approach towards axially chiral sulfoxide ligands via oxidative coupling. A range of products were obtained with excellent diastereoselectivities (up to >95:5) and 73-82% yields; some of those were converted into partially and fully desoxygenated derivatives. The prepared 4-tolyl-substituted ligands were successfully employed in the rhodium-catalyzed asymmetric addition of arylboronic acids to 2-cyclohexenone to furnish the corresponding products with 96-99% ee.