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 amino acids.
Department of Chemistry, Lebanon Valley College, Annville, Pennsylvania 17003, USA.
Alison E
AE
Hartman
Cheryl L
CL
Brophy
Julia A
JA
Cupp
Daniel K
DK
Hodge
Timothy J
TJ
Peelen
D000080:Acetals / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*
C496789:9-fluorenylmethoxycarbonyl; D000080:Acetals; D000596:Amino Acids; D005449:Fluorenes; D007097:Imines; D002244:Carbon