Addition to Sulfinylimines via Brook Rearrangement of Hydroxypropargylsilanes

Significance

A wide range of β-ketoamine ­derivatives 3 can be prepared with high levels of selectivity for both the amine and the alkene found in 3. The products obtained correspond to that ­resulting from an aza-Morita-Baylis-Hillman ­reaction. However, the advantage of the new procedure is that the geometry of the alkene is fully controlled, whereas the aza-MBH reaction typically leads to E/Z mixtures when R^¹ and R^³ are similar in steric bulk.