TY - JOUR
T1 - Iodide-Mediated [3 + 2]-Cycloaddition Reaction with N-Tosylaziridines and α,β-Unsaturated Ketones
AU - Nakagawa, Yuya
AU - Yamaguchi, Keigo
AU - Hosokawa, Seijiro
N1 - Funding Information:
We are grateful for the financial support from Fukuoka Naohiko Memorial Foundation and the Tokyo Biochemical Research Foundation. This work was also supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Frontier Research on Chemical Communications” (Grant Number 18H04632).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/6/4
Y1 - 2021/6/4
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.1c00532
DO - 10.1021/acs.joc.1c00532
M3 - Article
AN - SCOPUS:85108121143
SN - 0022-3263
VL - 86
SP - 7787
EP - 7796
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 11
ER -