Asymmetric Synthesis of N–N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations
N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone deriva...
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| Published in | Organic letters Vol. 24; no. 1; pp. 374 - 378 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Amer Chemical Soc
14.01.2022
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| Abstract | N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism. |
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| AbstractList | N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism.N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism. N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N-N axially chiral compounds by phase-transfer catalysis. A wide range of N-N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility of the protocol was proved by large-scale reaction and transformation of the product. Density functional theory calculations provide insight into the mechanism. |
| Author | Pan, Ming Zhao, Qun Shao, Ying-Bo Li, Xin |
| Author_xml | – sequence: 1 givenname: Ming surname: Pan fullname: Pan, Ming organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China – sequence: 2 givenname: Ying-Bo surname: Shao fullname: Shao, Ying-Bo organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China – sequence: 3 givenname: Qun surname: Zhao fullname: Zhao, Qun organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China – sequence: 4 givenname: Xin orcidid: 0000-0001-6020-9170 surname: Li fullname: Li, Xin organization: State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/34928616$$D View this record in MEDLINE/PubMed |
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| Snippet | N-N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for... N–N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for... |
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| Title | Asymmetric Synthesis of N–N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations |
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