Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2021 Oct 21

PMID 34672632

Citations 5

Authors

Jian-Qiang Zhao

Shun Zhou

Lei Yang

Hong-Yan Du

Yong You

Zhen-Hua Wang

Ming-Qiang Zhou

Wei-Cheng Yuan

Affiliations

Soon will be listed here.

Abstract

An enantioselective dearomative 1,3-dipolar cycloaddition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides with a bifunctional hydrogen-bonding thiourea catalyst was established, giving polyheterocyclic compounds in excellent results (up to 99% yield, >20:1 dr for all cases and up to 99% ee). The enantioselectivity could be reversed by the bifunctional hydrogen-bonding squaramide catalyst containing the same chiral source as in the thiourea catalyst. DFT calculations revealed the origin of the observed stereochemistry and the reversal of enantioselectivity.

Citing Articles

Engaging Isatins and Amino Acids in Multicomponent One-Pot 1,3-Dipolar Cycloaddition Reactions-Easy Access to Structural Diversity.

Zhao H, Zhao Y Molecules. 2023; 28(18).

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Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones.

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Stereoselective synthesis of CF-containing spirocyclic-oxindoles using -2,2,2-trifluoroethylisatin ketimines: an update.

Borah B, Veeranagaiah N, Sharma S, Patat M, Prasad M, Pallepogu R RSC Adv. 2023; 13(11):7063-7075.

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1,3-Dipolar cycloaddition reactions of isatin-derived azomethine ylides for the synthesis of spirooxindole and indole-derived scaffolds: recent developments.

Miankooshki F, Bayat M, Nasri S, Samet N Mol Divers. 2022; 27(5):2365-2397.

PMID: 35925529 DOI: 10.1007/s11030-022-10510-9.