Synfacts 2008(8): 0830-0830  
DOI: 10.1055/s-2008-1078554
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Addition of Organozinc Reagents to Vinyl Sulfones

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
J.-N. Desrosiers, W. S. Bechara*, A. Charette*
Université de Montréal, Canada
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

The authors have developed a simple protocol for the addition of organozinc reagents to vinyl sulfones. This procedure complements the already reported procedures including the reduction of β,β-dialkylsubstituted sulfones (J.-N. Desrosiers, A. B. Charette Angew. Chem. Int. Ed. 2007, 46, 5955; T. Llamas, R. Gómez Arrayás, J. C. Carretero Angew. Chem. Int. Ed. 2007, 46, 3329) and organometallic reagents to vinyl sulfones (K. Yoshida, T. Hayashi J. Am. Chem. Soc. 2003, 125, 2872; P. Mauleón, J. C. Carretero Org. Lett. 2004, 6, 3195). Furthermore, the authors have cleverly demonstrated the formation of β,β-dialkylsubstituted products with excellent enantioselectivities.