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atroposelective synthesis of 2-Arylindoles via Chiral Phosphoric Acid-Catalyzed Direct Amination of Indoles

Chinese Journal of Chemistry 2024年第7期42卷 731-735页

作者： Wen Bao Ye-Hui Chen Yu-Wei Liu Shao-Hua Xiang Bin Tan School of Pharmacy&StateKey Laboratory of Applied Organic Chemistry Lanzhou UniversityLanzhouGansu 730000China Shenzhen Grubbs Institute Department of ChemistrySouthern University of Science and TechnologyShenzhenGuangdong 518055China

Indole-based atropisomers are a very important class of axially chiral ***,the atroposelective synthesis of axially chiral 2-arylindole remains largely *** this study,we report the successful synthesis of atropisomeric 2-arylindoles using direct amination of indoles with p-quinonediimines in the presence of chiral phosphoric acid as a *** acts as an aminating reagent through formal polarity inversion of *** malonate group on the 2-aryl of 2-indoles was found to be essen-tial for high enantioselectivity of the *** could be due to the additional interaction between the ester group and the cata-lyst,as well as the intramolecular hydrogen *** findings provide a new strategy for the asymmetric construction of 2-arylindole atropisomers.

关键词： Chiral phosphoric acid Quinonediimines Direct amination Nucleophilic addition Asymmetric catalysis Enantioselectivity Axially chiral 2-arylindole atroposelective synthesis

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N-heterocyclic carbene-catalyzed atroposelective synthesis of axially chiral 5-aryl 2-pyrones from enals

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Science China Chemistry 2022年第10期65卷 1953-1961页

作者： Guanjie Wang Juhui Huang Linxue Zhang Jinna Han Xiaoxiang Zhang Jie Huang Zhenqian Fu Wei Huang Key Laboratory of Flexible Electronics&Institute of Advanced Materials Institute of Advanced SynthesisSchool of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources College of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Ningbo Institute Chongqing Technology innovation CenterFrontiers Science Center for Flexible Electronics(FSCFE)Northwestern Polytechnical UniversityXi’an 710072China

Axially chiral molecules have been widely used in inorganic,material and medicinal *** with well-established N-heterocyclic carbene(NHC)-catalyzed asymmetric construction of centrally chiral molecules,NHC-catalyzed atroposelective synthesis of axially chiral molecules remains largely ***,alkynyl acyl azolium intermediates were commonly used in constructing a heteroaryl ring to furnish axially enantioenriched *** inherent character of the intermediates often led to react with sterically hindered substrates ***,we have successfully disclosed the atroposelective synthesis of axially chiral heteroaryl-aryls from sterically hindered enols through the use of chiral NHCs as catalysts for highly enantioselective Coates-Claisen rearrangements via catalytically generatedα,β-unsaturated acyl *** approach will enable the concise synthesis of valuable tetra-ortho-substituted 2-pyrones in one step with good yield and chirality control.

关键词： N-heterocyclic carbene organocatalysis atroposelective synthesis 2-pyrones enals

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不对称轴手性化学（英文）

不对称轴手性化学（英文）

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中国化学会·第十六届全国有机合成化学学术研讨会

作者：谭斌南方科技大学

Axially chiral compounds(轴手性化合物)in which the chirality originates from highly sterically hindered rotation along a chiral axis rather than a stereogenic center with four different substituents have received much attention from chemists because of their widespread appearance in biologically active compounds and useful chiral ligands in asymmetric catalysis. Owing to the importance of this structural motif,the catalytic atroposelective construction of axially chiral scaffolds has been intensively investigated and great progress has been accomplished.2 However,the majority of methodologies in this field focused on the use of metal catalysis,whereas synthetic approaches involving organocatulysis have started to emerge only recently. We describe some advances from our group in organocatalytic atroposelective synthesis of axially chiral compounds involving the following strategies:enantioselective cross coupling of two aryl counterparts,asymmetric construction of an aromatic ring and kinetic resolution/desymmetrization and so on.

关键词： Axial Chirality Asymmetric Organocatalysis atroposelective synthesis

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