Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 19, Pages 3740-3746Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00546k
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Funding
- National Natural Science Foundation of China [21702189, 21672193, 21272218]
- Key Scientific and Technological Project of Henan Province [202102310004]
- China Ministry of Industry and Information Technology [Z135060009002]
- China Postdoctoral Science Foundation [2017M610458, 2018T110737]
- Postdoctoral Research Grant in Henan Province [001701006]
- Zhengzhou University of China
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A copper-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described. By using de novo design of P-stereogenic phosphines as ligands, spiro[pyrrolidin-3,3 ' -oxindole]s are generated in good to excellent yields with high asymmetric induction. A further reduced catalyst loading of 0.1 mol% is sufficient to achieve a satisfactory enantioselectivity of 90% ee. The DFT calculations suggest the second Michael addition of the 1,3-dipole to be the rate- and enantio-determining step. A key feature of this 1,3-dipolar cycloaddition is the wide substrate applicability, even with alkyl aldehyde-derived azomethine ylide; thus it has streamlined a highly enantioselective access to a new class of antiproliferative agents, MDM2-p53.
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