Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 19, Pages 9305-9312Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5018469
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Funding
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- PAPD
- Qing Lan Project of Jiangsu Province
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The first organocatalytic asymmetric inverse-electron-demand 1,3-dipolar cycloaddition (IED 1,3-DC) of N,N'-cyclic azomethine imines has been established in the presence of chiral phosphoric acid. This approach assembles N,N'-cyclic azomethine imines and o-hydroxystyrenes into chiral N,N-bicyclic pyrazolidin-3-one derivatives with the creation of two stereogenic centers, one of which is quaternary, in excellent diastereoselectivities and good enantioselectivities (up to >95:5 dr, 88:12 er). The investigation of the activation mode of the reaction revealed that the dual hydrogen-bonding interaction between the two substrates and the catalyst together with the conjugative effect initiated by the o-hydroxyl group played a crucial role in the designed IED 1,3-DC. This study will not only greatly enrich the underdeveloped research potential of catalytic asymmetric IED 1,3-DCs but will also facilitate the design of other enantioselective IED 1,3-DCs based on different activation modes.
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