Synthesis of N-tosyl-3,3,4-trisubstituted pyrrolidine derivatives starting from the Baylis–Hillman adducts via radical cyclization

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• 作者：Hyun Seung Lee ; Hoo Sook Kim ; Jeong Mi Kim ; Jae Nyoung Kim
• 关键词：Pyrrolidines ; Baylis– ; Hillman adducts ; Radical cyclization
• 刊名：Tetrahedron
• 出版年：2008
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：3 March 2008
• 卷：64
• 期：10
• 页码：2397-2404
• 文件大小：513 K

摘要

N-Tosyl-3,3-disubstituted-4-vinylpyrrolidine derivatives 3a–c were synthesized via radical cyclization from the modified Baylis–Hillman adducts 2. The required starting materials 2a–c were prepared in moderate yields from the Baylis–Hillman adducts in three steps: (i) acetylation of the Baylis–Hillman adducts, (ii) S_N2′ reaction with tosylamide to prepare 1, and (iii) alkylation with 1,4-dibromo-2-butene.