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

Yuya Nakagawa, Keigo Yamaguchi, Seijiro Hosokawa

Research output: Contribution to journalArticlepeer-review

Abstract

The [3 + 2]-cycloaddition reaction between N-tosylaziridines and α,β-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.

Original languageEnglish
Pages (from-to)7787-7796
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number11
DOIs
Publication statusPublished - 2021 Jun 4

ASJC Scopus subject areas

  • Organic Chemistry

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