Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with <i>ortho</i>-Quinone Methides

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (u...

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Autores principales: Si-Jia Liu, Man-Su Tu, Kai-Yue Liu, Jia-Yi Chen, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi
Formato: article
Lenguaje:EN
Publicado: MDPI AG 2021
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Acceso en línea:https://doaj.org/article/c1a76d72e781497ebb33bd808c65632d
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Sumario:Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with <i>ortho</i>-quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives.