Chiral phosphoric acid-catalyzed dual-ring formation for enantioselective construction of N-N axially chiral 3,3′-bisquinazolinones

In contrast with the well-developed C-C and C-N axial chirality, research focusing on the catalytically asymmetric synthesis of N-N axially chiral compounds is still limited. As a privileged subunit of many antibiotics, the synthesis of N-N axially chiral 3,3′-bisquinazolinones has not been updated...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 94; pp. 13131 - 13134
Main Authors Pu, Liang-Yuan, Zhang, Yu-Jiao, Liu, Wei, Teng, Fan
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 24.11.2022
Royal Society of Chemistry
Subjects
Antibiotics
Chemical compounds
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chirality
Enantiomers
Phosphoric acid
Physical Sciences
Science & Technology
ASYMMETRIC CONSTRUCTION
ARYLMALEIMIDES
DESIGN
BIARYL ATROPISOMERS
ATROPOSELECTIVE SYNTHESIS
RESOLUTION
ARYLATION
NONBIARYL
DESYMMETRIZATION
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Summary:In contrast with the well-developed C-C and C-N axial chirality, research focusing on the catalytically asymmetric synthesis of N-N axially chiral compounds is still limited. As a privileged subunit of many antibiotics, the synthesis of N-N axially chiral 3,3′-bisquinazolinones has not been updated with atroposelective construction. Herein, we firstly report a chiral phosphoric acid-catalyzed dual-ring formation strategy leading to the aforementioned compounds with good chemical yields and enantioselectivities. Notably, metal-free reaction conditions are another advantage of this procedure. An efficient, CPA-catalyzed, dual-ring formation strategy to construct a class of N-N axially chiral 3,3′-bisquinazolinones is reported for the first time. Notably, metal-free reaction conditions were also involved in this procedure.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
https://doi.org/10.1039/d2cc05172a
2204593
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05172a