Ahn Y, Cardenas G I, Yang J, Romo D
Department of Chemistry, P.O. Box 30012, Texas A&M University, College Station, Texas 77842-3012, USA.
Org Lett. 2001 Mar 8;3(5):751-4. doi: 10.1021/ol0155081.
[structure: see text]. In studies directed toward gymnodimine and related marine toxins, a single-pot variation of the Hua cyclic imine synthesis has been developed. The reaction involves generation of N-trimethylsilyl lactams in situ followed by alkyllithium addition leading directly to cyclic imines. Importantly, this reaction proceeds efficiently with highly hindered alpha,alpha-dialkyl lactams, provided 1,2-dimethoxyethane (DME) is used as solvent, leading to stable cyclic imines. Overall, this transformation allows a one-pot coupling of an alkyliodide and a lactam to give a cyclic imine.
[结构：见原文]。在针对裸甲藻毒素及相关海洋毒素的研究中，开发了一种华氏环亚胺合成的单步变体。该反应包括原位生成N-三甲基硅烷基内酰胺，随后加入烷基锂直接生成环亚胺。重要的是，只要使用1,2-二甲氧基乙烷（DME）作为溶剂，该反应就能高效地与高度受阻的α,α-二烷基内酰胺发生反应，生成稳定的环亚胺。总体而言，这种转化允许将烷基碘化物和内酰胺进行一锅法偶联以得到环亚胺。
