4.5 Article

Asymmetric [3+2] Annulations of Thioaurone and Aurone Derivatives for the Construction of Spiroheterocycles

期刊

ASIAN JOURNAL OF ORGANIC CHEMISTRY
卷 10, 期 4, 页码 784-787

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100078

关键词

spiroheterocycles; (thio)aurone; Morita– Baylis– Hillman carbonates; [3+2] annulation; allylic ylides

资金

  1. NSFC [21931006]

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Aurones and their analogues are useful in constructing valuable spiroheterocycles. The Morita-Baylis-Hillman carbonates of isatins can efficiently combine with thioaurones, aurones, or methyleneindolinones to produce a wide range of densely functionalized spiro-benzothiophene, -benzofuran, and bisspirooxindole frameworks with high yields and good to excellent stereoselectivity.
Aurones and their analogues are convenient two-atom units for the rapid construction of valuable spiroheterocycles. Here, we demonstrate that the Morita-Baylis-Hillman carbonates of isatins can be efficiently assembled with thioaurones, aurones, or even methyleneindolinones in a highly asymmetric [3+2] annulation manner, affording a broad spectrum of densely functionalized spiro-benzothiophene, -benzofuran and bisspirooxindole frameworks in high yields with good to excellent stereoselectivity.

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