Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes,Journal of the American Chemical Society

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Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-09-08 , DOI: 10.1021/jacs.0c07995
Peng Liu ₁ , Xiaoze Bao ₂ , Jean-Valère Naubron ₃ , Sara Chentouf ₃ , Stéphane Humbel ₁ , Nicolas Vanthuyne ₁ , Marion Jean ₁ , Laurent Giordano ₁ , Jean Rodriguez ₁ , Damien Bonne ₁

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An expedient synthesis of a new family of configurationally stable dioxa[6]helicenes was established using a sequential helicoselective organocatalyzed heteroannulation/eliminative aromatization via enantioenriched fused 2-nitro dihydrofurans featuring both central and helical chiralities. Starting from simple achiral precursors, a broad range of these previously unknown chiral heterocyclic scaffolds were obtained with good efficiency, and their aromatization proceeded with very high enantiopurity retention in most cases.

中文翻译：

中心和螺旋手性的同时控制：二氧杂环己烷[6]螺旋烯的便利螺旋选择性合成

使用顺序螺旋选择性有机催化杂环化/消除芳构化，通过具有中心和螺旋手性的对映体富集的稠合 2-硝基二氢呋喃，建立了构型稳定的二氧杂环 [6] 螺旋新家族的便利合成。从简单的非手性前体开始，以良好的效率获得了范围广泛的这些先前未知的手性杂环支架，并且在大多数情况下它们的芳构化以非常高的对映纯度保留进行。

更新日期：2020-09-08

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