Regio‐ und stereoselektive Synthese α,β‐disubstituierter Enamide durch Voraktivierung von Inamiden

Baldassari, Lucas L.; Torre, Aurélien de la; Li, Jing; Lüdtke, Diogo S.; Maulide, Nuno

doi:10.1002/ange.201709128

Angewandte Chemie

2017

DOI: 10.1002/ange.201709128

|View full text |Cite

Regio‐ und stereoselektive Synthese α,β‐disubstituierter Enamide durch Voraktivierung von Inamiden

Lucas L. Baldassari

Aurélien de la Torre

Jing Li

et al.

Abstract: Eine neue Strategie der Voraktivierung von Inamiden ermçglicht die Verwendung ansonsten inkompatibler Reagenzien und erlaubt somit die Herstellung a,b-disubstituierter Enamide mit hoher Regio-und Stereoselektivität. Mechanistische Analysen deuten auf die intermediäre Bildung einer Triflat-gebundenen Spezies hin, die als Reservoir für hochreaktive Keteniminiumionen fungiert und so die nachfolgende Addition metallorganischer Reagenzien ermçglicht. Hintergrundinformationen und die Identifikationsnummer (ORCID) ei… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2019

2023

Publication Types

Select...

Article5

Relationship

Self Cite1

Independent4

Authors

Journals

Cited by 12 publications

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids

Moskowitz

Wolf

2019

Angewandte Chemie

View full text Add to dashboard Cite

The highly enantioselective addition of terminal ynamides to a variety of isatins, catalyzed by a bisoxazolidine copper complex under mild, base‐free reaction conditions, is described. The reaction is broad in scope, scalable, applicable to unprotected isatins, and provides efficient access to 3‐hydroxyoxindoles carrying a tetrasubstituted chiral center with excellent yields and enantioselectivities. Synthetically versatile, multifunctional 3‐hydroxyindolinones are obtained by hydration, partial hydrogenation, or hydroxyacyloxylation of the ynamide moiety at room temperature and exhaustive hydrogenation followed by reductive detosylation and spontaneous cyclization affords cinchonamidine alkaloids.

show abstract

Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids

Moskowitz

Wolf

2019

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Efficient and Divergent Synthesis of α‐Halogenated Amides and Esters by Double Electrophilic Activation of Ynamides

Thilmany

Evano

2019

Angewandte Chemie

View full text Add to dashboard Cite

An efficient and modular entry to α‐halogenated amides and esters is reported. This reaction is based on an underestimated double electrophilic activation of ynamides sequentially involving highly reactive activated keteniminium and iminium ions. Upon simple reaction with HCl and an electrophilic halogenation reagent in the presence of water or an alcohol, a broad range of ynamides can be transformed, in a highly divergent manner, to α‐halo amides and esters with high efficiency and under mild conditions.

show abstract

Synthese von α‐Aminosäurederivaten durch hydrative Aminierung von Alkinen

et al. 2022

Self Cite

View full text Add to dashboard Cite

α-Aminosäurederivate sind Kernbestandteile jeglichen Lebens. Die Synthese von α-Aminocarbonyl/ carboxyl Verbindungen ist jedoch weiterhin eine Herausforderung für die organische Synthese. In dieser Arbeit berichten wir von einer praktischen Herstellungsmethode für α-Aminosäurederivate durch direkte hydrative Aminierung von aktivierten Alkinen mit Sulfinamiden unter milden Bedingungen. Computergestützte Untersuchungen legen nahe, dass eine [2,3]-sigmatrope Sulfoniumumlagerung der zentrale Schritt der Reaktion ist.

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.

Regio‐ und stereoselektive Synthese α,β‐disubstituierter Enamide durch Voraktivierung von Inamiden

Cited by 12 publications

References 78 publications

Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids

Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids

Efficient and Divergent Synthesis of α‐Halogenated Amides and Esters by Double Electrophilic Activation of Ynamides

Synthese von α‐Aminosäurederivaten durch hydrative Aminierung von Alkinen

Contact Info

Product

Resources

About