were observed in the acylation of amines, shown below. A similar protocol was developed for the kinetic resolution of indolines. Epoxidations and dihydroxylations The Sharpless epoxidation, developed by K. Barry Sharpless in 1980, has been utilized for the kinetic resolution of a racemic mixture of allylic alcohols. While extremely effective at resolving a number of allylic alcohols, this method has a number of drawbacks. Reaction times can run as long as 6 days, and the catalyst is not recyclable. However, the Sharpless asymmetric epoxidation kinetic resolution remains one of the most effective synthetic kinetic resolutions to date. A number of different tartrates can be used for the catalyst; a representative scheme is shown below utilizing diisopropyl tartrate. This method has seen general use on a number of secondary allylic alcohols. Sharpless asymmetric dihydroxylation has also seen use as a method for kinetic resolution. This method is not widely used, however, since the same resolution can be accomplished in different manners that are more economical. Additionally, the Shi epoxidation has been shown to affect kinetic resolution of a limited selection of olefins. This method is also not widely used, but is of mechanistic interest. Epoxide openings While enantioselective epoxidations have been successfully achieved utilizing Sharpless epoxidation, Shi epoxidation, and Jacobsen epoxidation, none of these methods allows for the efficient asymmetric synthesis of terminal epoxides, which are key chiral building blocks. Due to the inexpensiveness of most racemic terminal epoxides and their inability to generally be subjected to classical resolution, an effective kinetic resolution of terminal epoxides would serve as a highly important synthetic methodology. In 1996, Jacobsen and coworkers developed a methodology for the kinetic resolution of epoxides via nucleophilic ring-opening with attack by an azide anion. The (R,R) catalyst is shown. The catalyst could effectively, with loadings as low as 0.5 mol%, open the epoxide at the terminal position enantioselectively, yielding enantioenriched epoxide starting material and 1,2-azido alcohols. Yields are nearly quantitative and ee's were excellent (≥95% in nearly all cases). The 1,2-azido alcohols can be hydrogenated to give 1,2-amino alcohols, as shown below. In 1997, Jacobsen's group published a methodology which improved upon their earlier work, allowing for the use of water as the nucleophile in the epoxide opening. Utilizing a nearly identical catalyst, ee's in excess of 98% for both the recovered starting material epoxide and 1,2-diol product were observed. In the example below, hydrolytic kinetic resolution (HKR)