Abstract: Different protocols (lithium enolate reactions, fluoride catalyzed and Lewis acid mediated silyl ketene acetal reactions) were studied to achieve stereoselectivity in the aldol reactions of [gamma]-thiobutyrolactone: in all cases benzaldehyde showed a striking peculiarity compared to aliphatic aldehydes.
Abstract: A variety of chiral auxiliaries R*OH were prepared and tested for levels of asymmetric induction control in the "Mukaiyama-aldol" reaction of chiral silyl ketene acetals. Structural features required for high levels of control are discussed.
