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.
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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3-Pyrrolines, Azetidines, Organocatalysis