Asymmetric Dihydroxylation of Enamides to Give Quaternary Alcohols

Significance

The Sharpless dihydroxylation is one of the most predictable and reliable asymmetric transformations available. A major limitation is the use of 1,1-disubstituted alkenes, which often gives the tertiary alcohol containing products in low enantioselectivity. The authors seek an alternative route to these products by utilizing stereodefined β,β′-disubstituted enamides.