Department of Chemistry, Lebanon Valley College, Annville, Pennsylvania 17003, USA.
Org Lett. 2010 Jun 4;12(11):2464-7. doi: 10.1021/ol100494z.
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.
三甲基硅基卤化物活化 Fmoc 保护的 N,O-缩醛生成反应性中间体，能够有效地与各种烯胺加成。NMR 研究提供了证据，表明在溶液中形成了稳定的卤甲基氨基甲酸酯中间体。在广泛的烯胺亲核试剂范围内，包括环状和非环状酮衍生和醛衍生的烯胺，都能获得良好的产率。初步研究表明，烯胺加成通过协同的 S(N)2 型机制发生。
