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Synfacts 2011(9): 0981-0981  
DOI: 10.1055/s-0030-1260867
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Conjugate Boration of α,β-Unsaturated Sulfones

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
A. L. Moure, R. Gómez Arrayás*, J. C. Carretero*
Universidad Autónoma de Madrid, Spain
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Copper-catalyzed asymmetric β-boration of electron-deficient olefins represents one of the efficient pathways towards chiral boronates. However, despite the synthetic versatility of sulfones, α,β-unsaturated sulfones have not been considered as substrates for this transformation. In this paper such a methodology has been developed using Cu(I) complexes of (R,R)-Taniaphos and (R,S)-Josiphos. Subsequent in situ oxidation of the chiral boronates furnished a number of β-hydroxy sulfones with 77-97% ee.