Dual Brønsted‐acid Organocatalysis: Cooperative Asymmetric Catalysis with Combined Phosphoric and Carboxylic Acids,ChemCatChem

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Dual Brønsted‐acid Organocatalysis: Cooperative Asymmetric Catalysis with Combined Phosphoric and Carboxylic Acids
ChemCatChem ( IF 3.8 ) Pub Date : 2018-02-12 , DOI: 10.1002/cctc.201701698
Raja Mitra ₁ , Jochen Niemeyer ₁

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How can an assisting Brønsted‐acid be beneficial in asymmetric Brønsted‐acid catalysis? In this Minireview, we discuss selected examples of chiral organocatalysts that feature two acidic groups working cooperatively by virtue of intra‐ or intermolecular hydrogen‐bonding. In these systems, the assisting Brønsted‐acid can play different roles, ranging from simple hydrogen‐bond donation, to substrate‐binding or even as a nucleophilic reaction partner. By analysis of combined experimental, structural and theoretical data, we aim at developing a better understanding of the reaction mechanisms, which are largely influenced by the underlying intramolecular‐ and intermolecular catalyst‐substrate interactions. This may aid in the future development of more selective dual Brønsted‐acid organocatalysts for specific asymmetric transformations.

中文翻译：

双布朗斯台德酸有机催化：磷酸和羧酸组合的协同不对称催化

布朗斯台德酸助剂如何在不对称布朗斯台德酸催化中受益？在此Minireview中，我们讨论了手性有机催化剂的精选示例，这些手性有机催化剂的特征在于两个酸性基团通过分子内或分子间氢键协同作用。在这些系统中，布朗斯台德酸的辅助作用可以发挥不同的作用，从简单的氢键捐赠，底物结合甚至亲核反应伙伴都可以发挥作用。通过分析组合的实验，结构和理论数据，我们旨在更好地理解反应机理，这些机理很大程度上受潜在的分子内和分子间催化剂-底物相互作用的影响。这可能有助于将来开发用于特定不对称转化的更具选择性的布朗斯台德酸双有机催化剂。

更新日期：2018-02-12

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