Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes

Yang, Xue-Chun; Wu, Feng; Wu, Wen-Biao; Zhang, Xu; Feng, Jian-Jun

doi:10.1039/d4sc06334a

Chem. Sci.

2024

DOI: 10.1039/d4sc06334a

|View full text |Cite

Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes

Xue-Chun Yang,

Feng Wu,

Wen-Biao Wu

et al.

Abstract: We present the first enantioselective dearomative (3+3) cycloadditions of bicyclobutanes (BCBs) utilizing a chiral Lewis acid catalyst and bidentate chelating BCB substrates.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 110 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines

George,

Mindner,

Wittmer

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

A (3+3)‐cycloaddition to afford 2‐azabiyclo[3.1.1]heptanes was realized by reacting highly strained aryl bicyclo[1.1.0]butane (BCBs) carboxylates with tosylated aziridines. Under Sc(OTf)3 catalysis the transformation proceeded smoothly under mild conditions to the corresponding bicyclic products bearing at the bridgeheads of the embedded four‐membered ring aryl and ester moieties, respectively. This reaction is a rare example of a cycloaddition of two highly strained ring systems under Lewis acid catalysis. Mechanistic experiments provided insights into the reaction mechanism.

show abstract

Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines

George,

Mindner,

Wittmer

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Lewis Acid-Catalyzed 1,3-Dipolar Cycloaddition of Bicyclobutanes with Isatogens: Access to Tetracyclic 2-Oxa-3-azabicyclo[3.1.1]heptanes

Deswal,

Das,

Sarkar

et al. 2024

JACS Au

View full text Add to dashboard Cite

The 'escape from flatland' concept has gained significant traction in modern drug discovery, emphasizing the importance of three-dimensional molecular architectures, which serve as saturated bioisosteres of benzenoids. Bicyclo[1.1.0]butanes (BCBs), known for their high ring strain and numerous reactivities, offer a simple yet effective method for synthesizing these bicyclic frameworks. Although (3 + 2) annulations involving BCBs have been extensively studied, the 1,3-dipolar cycloaddition of BCBs leading to (3 + 3) annulation has received limited attention. Herein, we report the Lewis acid-catalyzed 1,3-dipolar cycloaddition of BCBs with isatogens allowing the synthesis of biologically relevant tetracyclic 2-oxa-3-azabicyclo[3.1.1]heptanes. Moreover, the reaction can be performed in a one-pot process by the in situ generation of isatogens from 2-alkynylated nitrobenzenes. Additionally, preliminary mechanistic and photophysical studies of the (3 + 3) annulated products and experiments toward the asymmetric version of this reaction are also provided.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Enantioselective dearomative formal (3+3) cycloadditions of bicyclobutanes with aromatic azomethine imines: access to fused 2,3-diazabicyclo[3.1.1]heptanes

Abstract: We present the first enantioselective dearomative (3+3) cycloadditions of bicyclobutanes (BCBs) utilizing a chiral Lewis acid catalyst and bidentate chelating BCB substrates.

Cited by 2 publications

References 110 publications

Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines

Double Strain‐Release (3+3)‐Cycloaddition: Lewis Acid Catalyzed Reaction of Bicyclobutane Carboxylates and Aziridines

Lewis Acid-Catalyzed 1,3-Dipolar Cycloaddition of Bicyclobutanes with Isatogens: Access to Tetracyclic 2-Oxa-3-azabicyclo[3.1.1]heptanes

Contact Info

Product

Resources

About