期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 1, 页码 512-520出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo502516e
关键词
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资金
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- undergraduate students project of Jiangsu Province
- JSNU, PAPD of Jiangsu Province and
- Cling Lan Project
The first catalytic asymmetric 1,3-dipolar cycloadditions (1,3-DCs) of isatin-derived azomethine ylide with allenes have been established, which efficiently assembly isatins, amino-esters and 2,3-allenoate into enantioenriched spiro[indoline-3,2'-pyrrole] derivatives with a quaternary stereogenic center in generally high enantioselectivities (80-98% ee). In this allene-involved 1,3-DC, an unexpected spirooxindole framework bearing an intra-annular C-C double bond was generated, which is quite different from previously reported 1,3-DCs of allenes. This approach not only confronted the great challenge in using allenes as dipolarophiles of 1,3-DCs, but also provided a unique strategy of using allenes as equivalents of alkynes to construct spiro[indoline-3,2'-pyrrole] structure. Besides, this reaction also represents the first catalytic asymmetric ketone-involved 1,3-DCs of allenes, which will also greatly enrich the research contents of 1,3-DCs, the chemistry of allenes as well as the synthetic methods of spirooxindoles.
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