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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Bibliographic Details
Published inOrganic letters Vol. 24; no. 1; pp. 374 - 378
Main Authors Pan, Ming, Shao, Ying-Bo, Zhao, Qun, Li, Xin
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 14.01.2022
Subjects
alkylation
catalytic activity
Chemistry
Chemistry, Organic
density functional theory
drugs
Physical Sciences
Science & Technology
stereoselective synthesis
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c04028