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Activation of Fmoc-Protected N,O-Acetals Using Trimethylsilyl Halides: Mechanistic and Synthetic Studies

  作者 BOAZ NICHOLAS C; BAIR NATHANIEL C; LE THANH T; PEELEN TIMOTHY J  
  选自 期刊  Organic Letters;  卷期  2010年12-11;  页码  2464-2467  
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[摘要]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.

 
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