Asymmetric synthesis of N-N axially chiral compounds <i>via</i> organocatalytic atroposelective <i>N</i>-acylation.

Lin, Wei; Zhao, Qun; Li, Yao; Pan, Ming; Yang, Chen; Yang, Guo-Hui; Li, Xin

Asymmetric synthesis of N-N axially chiral compounds via organocatalytic atroposelective N-acylation.

Lin, Wei; Zhao, Qun; Li, Yao; Pan, Ming; Yang, Chen; Yang, Guo-Hui; Li, Xin.

Afiliación

Lin W; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Zhao Q; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Li Y; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Pan M; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Yang C; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Yang GH; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.
Li X; State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China xin_li@nankai.edu.cn.

Chem Sci ; 13(1): 141-148, 2021 Dec 22.

Article en En | MEDLINE | ID: mdl-35059162

RESUMEN

Compared with the well-developed C-C and C-N axial chirality, the asymmetric synthesis of N-N axial chirality remains elusive and challenging. Herein we report the first atroposelective N-acylation reaction of quinazolinone type benzamides with cinnamic anhydrides for the direct catalytic synthesis of optically active atropisomeric quinazolinone derivatives. This reaction features mild conditions and a broad substrate scope and produces N-N axially chiral compounds with high yields and very good enantioselectivities. Besides, the synthetic utility of the protocol was proved by a large scale reaction, transformation of the product and the utilization of the product as an acylation kinetic resolution reagent. Moreover, DFT calculations provide convincing evidence for the interpretation of stereoselection.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2021 Tipo del documento: Article Pais de publicación: Reino Unido

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