Asymmetric α-Alkylation of Acyclic Tin Enolates

Significance

The catalytic enantioselective α-alkylation of enolates which lack a chelating or tethering functionality remains a difficult task in organic synthesis. The authors recently reported a stereoselective α-alkylation of cyclic tin enolates (J. Am. Chem. Soc. 2005, 127, 62-63) and have now successfully extended this method to simple acyclic tin enolates, where the E/Z-isomers of the enolate interconvert in a resolution process before reacting with the electrophile to obtain α-chiral carbonyl compounds with three different alkyl groups.