Friday, 6 October 2006
South Ballroom (Binghamton Regency Hotel and Conference Center)
374

The development of reactions of silyl enol ethers with Fmoc-protected acyl imines

Julia A. Cupp and Timothy J. Peelen. Lebanon Valley College, Annville, PA

Current syntheses of Fmoc-protected amines, which are useful in solid phase peptide synthesis and combinatorial chemistry, typically require numerous protecting and deprotecting steps. Our research is focused on the direct synthesis of Fmoc-protected amines through the addition of weakly basic nucleophiles with Fmoc-protected acyl imines. Toward this goal, we report the additions of silyl enol ethers to Fmoc-protected N,O-acetal 1, which is a versatile electrophile for C-C bond forming reactions. Screening of Lewis acids and reaction conditions led to a ZnCl2-catalyzed reaction that provides a variety of β-amino ketones in excellent yields.


Back to Undergraduate Research (Posters)
Back to The 34th Northeast Regional Meeting (October 5-7 2006)