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Chiral disulfonimides: a versatile template for asymmetric catalysis.
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2020-08-31 , DOI: 10.1039/d0ob01742f
Meghan C Benda 1 , Stefan France
Affiliation  

Since the emergence of pseudo-C2-symmetric chiral phosphoric acids (CPA), much work has been done to utilize these systems in stereoselective, organocatalytic processes. Despite the success in this field, reasonably basic substrates such as imines are often required to achieve appreciable activation. In order to access a wider variety of potential reaction partners, many related organocatalysts with enhanced Brønsted acidity have since been developed. Chiral disulfonimides (DSIs) have materialized as one such powerful class of organocatalysts and have been shown to expand the list of potential substrates to include aldehydes and ketones via Brønsted, Lewis, or bifunctional acid activation. This versatility renders DSIs amenable to an impressive scope of reaction types, typically with remarkable stereoselectivity induced by asymmetric counteranion-directed catalysis (ACDC). This review serves to provide a complete analysis of the successful applications, mechanistic insights, and unmet challenges exhibited to date in DSI-catalyzed and -assisted processes.

中文翻译:

手性二磺酰亚胺:不对称催化的通用模板。

自从出现假C 2对称手性磷酸 (CPA) 以来,已经进行了大量工作以在立体选择性有机催化过程中利用这些系统。尽管在该领域取得了成功,但通常需要合理的碱性底物(例如亚胺)来实现可观的活化。为了获得更广泛的潜在反应伙伴,已经开发了许多具有增强布朗斯台德酸度的相关有机催化剂。手性二磺酰亚胺 (DSI) 已成为一类如此强大的有机催化剂,并已被证明可以通过以下方式扩展潜在底物的列表以包括醛和酮Brønsted、Lewis 或双功能酸活化。这种多功能性使 DSI 能够适应令人印象深刻的反应类型范围,通常具有由不对称反阴离子定向催化 (ACDC) 诱导的显着立体选择性。本综述旨在对迄今为止在 DSI 催化和辅助过程中展示的成功应用、机理见解和未解决的挑战进行全面分析。
更新日期:2020-10-07
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