Cycloaddition of Alkynyl Ketones with N-Tosylimines Catalyzed by Bu₃P and DMAP: Synthesis of Highly Functionalized Pyrrolidines and Azetidines

Ling-Guo Meng, Peijie Cai, Qingxiang Guo and Song Xue*

*Department of Chemistry, University of Science and Technology of China, Hefei 230026, Peoples Republic of China, Email: xuesongustc.edu.cn

L.-G. Meng, P. Cai, Q. Guo, S. Xue, J. Org. Chem., 2008, 73, 8491-8496.

DOI: 10.1021/jo801687v

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Abstract

The reaction of alkynyl ketones with N-tosylimines catalyzed by Bu₃P at room temperature in toluene gives highly functionalized 3-pyrrolines in very good yields. When DMAP was used in place of Bu₃P as catalyst to facilitate the cycloaddition, completely substituted azetidines were produced in moderate yields in CH₂Cl₂.

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Key Words

3-Pyrrolines, Azetidines, Organocatalysis

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ID: J42-Y2008-3210