Friday, 6 October 2006
South Ballroom (Binghamton Regency Hotel and Conference Center)
371

Development of novel C-C bond-forming reactions for the efficient synthesis of Fmoc-protected amines

Alison E. Hartman and Timothy J. Peelen. Lebanon Valley College, Annville, PA

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.


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