Conjugate Addition of Grignard Reagents to α,β-Unsaturated Sulfones

Significance

Sulfones bearing a stereocenter at the β-position represent an important class of synthetically useful synthons. Previously reported procedures employ the conjugate reduction of β,β-disubstituted α,β-unsaturated sulfones (T. Llamas, R. G. Arrays, J. C. Carretero Angew. Chem. Int. Ed. 2007, 46, 3329; J.-N. Desrosiers, A. B. Charette Angew. Chem. Int. Ed. 2007, 46, 5955). This report discusses the conjugate addition of organometallic reagents to to α,β-unsaturated sulfones as an alternative route to access these products.

Review: S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard, B. L. Feringa Chem. Rev. 2008, 108, 2824-2852.