We report a method for the synthesis of Fmoc-protected amines, which are useful in solid phase peptide synthesis and combinatorial chemistry. The new method was developed with the goal of eliminating the numerous protecting/deprotecting steps from previously reported methods to produce a green and atom economical synthesis. Toward this goal, we have developed a simple synthesis of Fmoc-protected amine
1, which forms acyl imine
2 in the presence of Lewis acids. Imine
2 is a versatile electrophile for C-C bond forming reactions. We have demonstrated and optimized this reactivity in several C-C bond forming reactions, including the additions of allylsilanes, silyl enol ethers, and enamines.
