Box-copper catalyzed asymmetric inverse-electron-demand oxa-hetero-Diels–Alder reaction for efficient synthesis of spiro pyranyl-oxindole derivatives
Literature Information
Publication Date
2021-02-26
DOI
10.1039/D0QO01407A
Impact Factor
5.281
Authors
Nai-Kai Li, Bing-Bing Sun, Jun-Bo Chen, Hao-Di Yang, Bai-Lin Wang, Jie-Qiang Yu, Xing-Wang Wang, Zheng Wang
View Original
Abstract
Spiro oxindole-pyran backbones are structural motifs widely occurring in natural products and bioactive synthetic compounds. In this paper, we present the asymmetric catalytic synthesis of three series of spirooxindole-pyran derivatives via an inverse-electron-demand oxa-hetero-Diels–Alder (IEDDA) reaction in the presence of 2.5–10 mol% of chiral bisoxazoline/copper(II) complexes as Lewis acid catalysts. Under mild reaction conditions, the IEDDA reactions of isatin-derived β,γ-unsaturated α-ketoesters with some dienophiles, such as 2,3-dihydrofuran, 3,4-dihydro-2H-pyran and ortho-vinylphenols, respectively, furnished the corresponding chiral spiro oxindole-pyrans in excellent yields with excellent diastereo- and enantioselectivities.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure](https://static.chemtradehub.com/structs/797/79793-00-3-de16.webp "4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride structure")
4-[2-(Trichlorosilyl)ethyl]benzenesulfonyl chloride
CAS Number:
79793-00-3
Molecular Formula:
C8H8Cl4O2SSi
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