Addition of carbon-based nucleophiles to Fmoc-protected acyl iminium ions.

Abstract

Weakly basic carbon nucleophiles add efficiently to a Fmoc-protected N,O-acetal compound. The new reactions highlight 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. 
DOI: 10.1021/jo8027714

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