title: Activation of Fmoc-protected N,O-acetals using trimethylsilyl halides: mechanistic and synthetic studies.
abstract: Trimethylsilyl halide activation of Fmoc-protected N,O-acetals yields reactive intermediates capable of efficiently adding to a variety of enamines. NMR studies have provided evidence that a stable halomethyl carbamate intermediate forms in solution. Good yields are obtained over a broad range of enamine nucleophiles encompassing both cyclic and acyclic ketone-derived and aldehyde-derived enamines. Preliminary studies suggest that the enamine additions occur through a concerted, S(N)2-type mechanism.
authors.affiliation: Department of Chemistry, Lebanon Valley College, Annville, Pennsylvania 17003, USA.
authors.forename: Nicholas C
authors.initials: NC
authors.lastname: Boaz
authors.forename: Nathaniel C
authors.initials: NC
authors.lastname: Bair
authors.forename: Thanh T
authors.initials: TT
authors.lastname: Le
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Peelen
mesh_terms: D000080:Acetals / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005449:Fluorenes / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C496789:9-fluorenylmethoxycarbonyl; D000080:Acetals; D005449:Fluorenes; D006846:Hydrocarbons, Halogenated; D014297:Trimethylsilyl Compounds