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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2009-05, Vol.74 (10), p.3952-3954
Hauptverfasser: Hartman, Alison E, Brophy, Cheryl L, Cupp, Julia A, Hodge, Daniel K, Peelen, Timothy J
Format: Artikel
Sprache:eng
Schlagworte:
Acetals - chemistry
Aliphatic compounds
Amino Acids - chemistry
Carbon - chemistry
Chemistry
Exact sciences and technology
Fluorenes - chemistry
Imines - chemistry
Organic chemistry
Preparations and properties
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo8027714