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

文献情報

出版日 2021-02-26

DOI 10.1039/D0QO01407A

インパクトファクター 5.281

著者

Nai-Kai Li, Bing-Bing Sun, Jun-Bo Chen, Hao-Di Yang, Bai-Lin Wang, Jie-Qiang Yu, Xing-Wang Wang, Zheng Wang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 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

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

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