학술논문
Activation of Fmoc-Protected N,O-Acetals Using Trimethylsilyl Halides: Mechanistic and Synthetic Studies.
Document Type
Article
Source
Subject
*HALIDES
*INTERMEDIATES (Chemistry)
*NUCLEAR magnetic resonance
*NUCLEOPHILIC reactions
*ALDEHYDES
*ENAMINES
*SOLUTION (Chemistry)
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Language
ISSN
1523-7060
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, SN2-type mechanism. [ABSTRACT FROM AUTHOR]