Lewis acid-catalyzed formal 1,3-aminomethyl migration

Shibata, Suzuka; Amano, Kazuko; Kojima, Tatsuhiro; Mori, Keiji

doi:10.1039/d3cc03059h

Chem. Commun.

2023

DOI: 10.1039/d3cc03059h

|View full text |Cite

Lewis acid-catalyzed formal 1,3-aminomethyl migration

Suzuka Shibata

Kazuko Amano

Tatsuhiro Kojima

et al.

Abstract: Here we report a Lewis acid-catalyzed 1,3-aminomethyl migration rection. When δ-amino acid derivatives were treated with a catalytic amount of Sc(OTf)3, 1,3-migration of the aminomethyl group proceeded smoothly to afford...

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...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Li,

Guo,

Liu

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols and 2‐allylphenols as substrates in the presence of Bi(OTf)3 and AgOTf is described. This Lewis acid catalyzed [3 + 2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐exo‐trig cyclization, 5‐endo‐trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen‐containing tricyclic skeletons in moderate‐to‐excellent yields. In addition, most of the obtained compounds exhibited anti‐tumor activities against three types of human cancer cell lines in vitro, including Caco‐2 colon cancer cells, MCF‐7 breast cancer cells, and Hepg‐2 liver cancer cells.

show abstract

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Li,

Guo,

Liu

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

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.

Lewis acid-catalyzed formal 1,3-aminomethyl migration

Abstract: Here we report a Lewis acid-catalyzed 1,3-aminomethyl migration rection. When δ-amino acid derivatives were treated with a catalytic amount of Sc(OTf)3, 1,3-migration of the aminomethyl group proceeded smoothly to afford...

Cited by 1 publication

References 64 publications

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities

Contact Info

Product

Resources

About