Meng Ling-Guo, Cai Peijie, Guo Qingxiang, Xue Song
Department of Chemistry, University of Science and Technology of China, Hefei 230026, People's Republic of China.
J Org Chem. 2008 Nov 7;73(21):8491-6. doi: 10.1021/jo801687v. Epub 2008 Oct 8.
Cycloadditions of alkynyl ketones with N-tosylimines catalyzed by Lewis bases to synthesize azetidines and pyrrolidines were systematically described. In the reaction of alkynyl ketones with N-tosylimines catalyzed by Bu3P at room temperature in toluene, highly functionalized pyrrolidines were formed in good to excellent yields. When DMAP was used in place of Bu3P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate to good yields in CH2Cl2. Both cyclization reactions proceeded smoothly with complete stereoselectivity. The scope and limitations of these cycloaddition reactions were also investigated.
系统地描述了在路易斯碱催化下炔基酮与N-甲苯磺酰亚胺的环加成反应，用于合成氮杂环丁烷和吡咯烷。在室温下，于甲苯中由三丁基膦催化炔基酮与N-甲苯磺酰亚胺的反应中，能以良好至优异的产率生成高度官能化的吡咯烷。当使用4-二甲氨基吡啶代替三丁基膦作为催化剂促进环加成反应时，在二氯甲烷中能以中等至良好的产率生成完全取代的氮杂环丁烷。这两种环化反应均顺利进行，具有完全的立体选择性。还研究了这些环加成反应的适用范围和局限性。
