Iodide-Mediated [3+2]-Cycloaddition Reaction with N-Tosylaziridines and α,β-Unsaturated Ketones

被引：2

作者：

Nakagawa, Yuya ^{[1
]}

Yamaguchi, Keigo ^{[1
]}

Hosokawa, Seijiro ^{[1
]}

机构：

[1] Waseda Univ, Dept Appl Chem, Fac Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 11期

关键词：

ASYMMETRIC-SYNTHESIS; PHENYLAZIRIDINE; CYCLOADDITIONS; AZIRIDINES;

D O I：

10.1021/acs.joc.1c00532

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3 + 2]-cycloaddition reaction between N-tosylaziridines and alpha,beta-unsaturated ketones was promoted with lithium iodide. The reaction proceeded under mild conditions to provide N-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.

引用

页码：7787 / 7796

页数：10

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