Nakagawa Yuya, Yamaguchi Keigo, Hosokawa Seijiro
Department of Applied Chemistry, Faculty of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
J Org Chem. 2021 Jun 4;86(11):7787-7796. doi: 10.1021/acs.joc.1c00532. Epub 2021 May 25.
The [3 + 2]-cycloaddition reaction between -tosylaziridines and α,β-unsaturated ketones was promoted with lithium iodide. The reaction proceeded under mild conditions to provide -tosylpyrrolidines. Quaternary carbon-possessing 3,3-disubstituted pyrrolidines including spiro compounds were afforded in high yields. A simple procedure with easy to handle reagents makes this reaction concise. The intramolecular version of this reaction was applied to synthesize tropane skeletons.
对甲苯磺酰基氮丙啶与α,β-不饱和酮之间的[3 + 2]环加成反应在碘化锂的促进下进行。该反应在温和条件下进行，生成对甲苯磺酰基吡咯烷。包括螺环化合物在内的具有季碳的3,3-二取代吡咯烷以高产率得到。使用易于操作的试剂的简单方法使该反应简洁明了。该反应的分子内版本被应用于合成托烷骨架。
