How achiral Brønsted acid is involved in co-catalyst model with chiral phosphoric acid for construction of quaternary carbon stereocenter

Li, Zi-Hao; Zhou, Jia; Liu, Chang; Tan, Fu-Xin; Wang, Le; Zhu, Guo-Dong; Zhang, Shu-Yu

doi:10.1016/j.checat.2024.100918

Chem Catalysis

2024

DOI: 10.1016/j.checat.2024.100918

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How achiral Brønsted acid is involved in co-catalyst model with chiral phosphoric acid for construction of quaternary carbon stereocenter

Zi-Hao Li,

Jia Zhou,

Chang Liu

et al.

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Cited by 3 publications

References 84 publications

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B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

Wei,

Wang,

et al. 2024

Chemistry A European J

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Here we report B(C6F5)3/CPA‐catalyzed enantioselective aza‐Diels–Alder reaction of 3,3‐difluoro‐2‐Aryl‐3H‐indoles with unactivated dienes to access chiral 10,10‐difluoro‐tetrahydropyrido[1,2‐a]indoles. This protocol allows the formation of pyrazole‐based C2‐quaternary indolin‐3‐ones with high enantioselectivities and regioselectivities. Moreover, gram‐scale synthesis of the 10,10‐difluoro‐tetrahydropyrido[1,2‐a]indole skeleton was successfully achieved without any reduction in both yield and enantioselectivity.

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B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

Wei,

Wang,

et al. 2024

Chemistry A European J

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Synthesis of Fluorine‐Containing C2‐Tetrasubstituted Indolin–3‐ones via Rapid Incorporation of Difluoroacetate Radical Into 2‐Aryl‐3H‐indol‐3‐ones

Li,

Zhao,

et al. 2024

Eur J Org Chem

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Here, we have successfully achieved the addition of difluoroacetate radicals to 2‐aryl‐3H‐indol‐3‐ones, enabling various difluoroalkylations of C2‐tetrasubstituted 2‐aryl indolin‐3‐ones in a highly efficient and economical manner. It is worth mentioning that these difluoroalkylation compounds can be easily transformed into various derivatives under mild reaction conditions. Control experiments suggest the involvement of ethyl difluoroacetate radical species in the reaction.

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Enantioselective Aminative Dearomatization of Indoles via Electrophilic 1,6-Addition of p-Quinone Diimides (p-QDIs)

Subba,

Sahoo,

Khajuria

et al. 2024

Org. Lett.

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Herein we report the first use of p-quinone diimide for the aminative dearomatization of 2,3-disubstituted indoles to furnish C3 aza-quaternary chiral indolenines. This approach, which proceeds via an electrophilic 1,6-addition of p-quinone diimide, allows the synthesis of an array of optically active aza-quaternary indolenines with high yields and excellent enantioselectivities. A one-pot approach of the same has also been established to further improve the synthetic accessibility of this protocol.

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How achiral Brønsted acid is involved in co-catalyst model with chiral phosphoric acid for construction of quaternary carbon stereocenter

Cited by 3 publications

References 84 publications

B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

Synthesis of Fluorine‐Containing C2‐Tetrasubstituted Indolin–3‐ones via Rapid Incorporation of Difluoroacetate Radical Into 2‐Aryl‐3H‐indol‐3‐ones

Enantioselective Aminative Dearomatization of Indoles via Electrophilic 1,6-Addition of p-Quinone Diimides (p-QDIs)

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How achiral Brønsted acid is involved in co-catalyst model with chiral phosphoric acid for construction of quaternary carbon stereocenter

Cited by 3 publications

References 84 publications

B(C6F5)3/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

B(C6F5)3/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

Synthesis of Fluorine‐Containing C2‐Tetrasubstituted Indolin–3‐ones via Rapid Incorporation of Difluoroacetate Radical Into 2‐Aryl‐3H‐indol‐3‐ones

Enantioselective Aminative Dearomatization of Indoles via Electrophilic 1,6-Addition of p-Quinone Diimides (p-QDIs)

Contact Info

Product

Resources

About

B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes

B(C₆F₅)₃/CPA‐Catalyzed Aza‐Diels‐Alder Reaction of 3,3‐Difluoro‐2‐Aryl‐3H‐indoles and Unactivated Dienes