Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

被引：0
作者：
Butt, Smaher E. [1 ]
Kepski, Konrad [1 ]
Sotiropoulos, Jean-Marc [2 ]
Moran, Wesley J. [3 ]
机构：
[1] Univ Huddersfield, Dept Phys & Life Sci, Queensgate, Huddersfield HD1 3DH, England
[2] Univ Pau & Pays Adour, IPREM, CNRS UMR 5254, Technopole Helioparc, 2 Ave President Pierre Angot, Pau 09, France
[3] Keele Univ, Sch Pharm & Bioengn, Keele ST5 5JX, Staffordshire, England
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷
基金：
英国工程与自然科学研究理事会;
关键词：
cyclization; DFT; hypervalent iodine; mechanism; proline; DERIVATIVES; MICHAEL;
D O I：
10.3762/bjoc.20.209
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A change in mechanism was observed in the hypervalent iodine-mediated cyclization of N-alkenylamides when the carbon chain between the alkene and the amide increased from two to three atoms. In the latter case, cyclization at the amide nitrogen to form the pyrrolidine ring was favored over cyclization at the amide oxygen. A DFT study was undertaken to rationalize the change in mechanism of this cyclization process. In addition, reaction conditions were developed, and the scope of this cyclization studied.
引用
收藏
页码：2455 / 2460
页数：6
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