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Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization-Coupling Reactions: An Efficient Synthesis of 3-Arylmethylpyrrolidines

Chi-Wan Lee, Kyung Seok Oh, Kwang S. Kim* and Kyo Han Ahn

*Department of Chemistry, Pohang University of Science and Technology, San 31 Hyoja-dong, Pohang 790-784, Republic of Korea, Email: kimksunist.ac.kr

C.-W. Lee, K. S. Oh, K. S. Kim, K. H. Ahn, Org. Lett., 2000, 2, 1213-1216.

DOI: 10.1021/ol0056426 (free Supporting Information)


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Abstract

A palladium-catalyzed cascade cyclization-coupling reaction with suppressed β-hydride elimination provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual β-elimination.

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Key Words

pyrrolidines


ID: J54-Y2000