N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl-Containing Amines and Amino Acids of Pharmaceutical Importance

Synthetic methods for the preparation of compounds containing trifluoromethyl groups are in extremely high demand in nearly every sector of the chemical industry. Over the last several years the chemistry of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine has undergone particular development. Currently, it is commonly used as a versatile reagent for general asymmetric synthesis of trifluoromethyl-containing amines and amino acids of pharmaceutical potential. This review provides a critical and comprehensive overview of synthetic applications of this reagent as well as of several relevant analogues, such as aldimines containing -CHF2, -CClF2, -CBrF2, and -CF2P(O)(OEt)(2) groups and N-tert-butylsulfinyl-3,3,3-trifluoromethyl-substituted ketimines. Where it is possible, we emphasize the structural novelty and pharmaceutic value of the products obtainable by application of these reagents.