Box-copper catalyzed asymmetric inverse-electron-demand oxa-hetero-Diels–Alder reaction for efficient synthesis of spiro pyranyl-oxindole derivatives

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) r...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-05, Vol.8 (9), p.2009-2018
Main Authors: Li, Nai-Kai, Bing-Bing Sun, Jun-Bo, Chen, Hao-Di, Yang, Bai-Lin, Wang, Jie-Qiang, Yu, Xing-Wang, Wang, Wang, Zheng
Format: Article
Language:English
Subjects:
Asymmetry
Catalysts
Chemical synthesis
Coordination compounds
Copper
Copper compounds
Crystallography
Diels-Alder reactions
Ketoesters
Lewis acid
Natural products
Organic chemistry
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo01407a