Synthesis of axially chiral thiourea by NHC-catalyzed desymmetrizative amidation†

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-09-30 DOI:10.1039/D4GC03113J

Yingtao Wu, Xin Guan, Kehan Jiao, Huaqiu Zhao, Mingrui Li, Jiaqiong Sun, Guangfan Zheng and Qian Zhang

引用次数: 0

Abstract

Chiral thiourea, with a double hydrogen-bonding motif, has emerged as an attractive structural template for asymmetric catalysis. Catalytic synthesis of enantioenriched NH-free thiourea via functionalization of easily accessible racemic thiourea is highly desirable, albeit a formidable challenge. We herein describe NHC-catalyzed desymmetrizative amidation of axially biaryl dialdehydes, providing structurally diverse axially chiral thiourea. Sequential kinetic resolution improves the enantioenrichment of the desymmetrization product, dramatically expanding the range of applicable substrates. This strategy features a broad substrate scope and extremely excellent enantioselectivity. NHC-catalyzed desymmetrizative amidation of axially prochiral biaryl dialdehydes provides modular platforms for synthesizing challenging axially chiral thiourea and derivatives.

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通过 NHC 催化的非对称酰胺化反应合成轴向手性硫脲

具有双氢键结构的手性硫脲已成为一种极具吸引力的不对称催化结构模板。通过对容易获得的外消旋硫脲进行官能化催化合成不含 NH 的对映体硫脲是非常理想的，尽管这是一项艰巨的挑战。我们在此描述了 NHC 催化的轴向双芳基二醛的非对称酰胺化反应，从而提供了结构多样的轴向手性硫脲。顺序动力学解析提高了去对称化产物的对映体富集度，极大地扩展了适用底物的范围。该策略具有广泛的底物范围和极其出色的对映选择性。NHC 催化的轴向手性双芳基二醛的非对称酰胺化为合成具有挑战性的轴向手性硫脲及其衍生物提供了模块化平台。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.