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Addition of Carbon-Based Nucleophiles to Fmoc-Protected Acyl Iminium Ions

Alison E. Hartman, Cheryl L. Brophy, Julia A. Cupp, Daniel K. Hodge and Timothy J. Peelen*

*Department of Chemistry, Lebanon Valley College, Annville, Pennsylvania 17003, Email:

A. E. Hartman, C. L. Brophy, J. A. Cupp, D. K. Hodge, T. J. Peelen, J. Org. Chem., 2009, 74, 3952-3954.

DOI: 10.1021/jo8027714 (free Supporting Information)

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Weakly basic carbon nucleophiles add efficiently to a Fmoc-protected N,O-acetal. The new reactions shows the compatibility of the Fmoc protecting group with moderately basic reaction conditions and should serve as a model for the development of more efficient syntheses of Fmoc-protected amino acids.

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proposed reaction pathway

Key Words

Fmoc-protected Amines, β-Amino Ketones

ID: J42-Y2009-1530