Intramolecular hydroalkylation of in situ-generated bis-homoallylic chiral piperazinonates
Document Type
Oral Presentation
Campus where you would like to present
Ellensburg
Event Website
https://digitalcommons.cwu.edu/source
Start Date
15-5-2019
End Date
15-5-2019
Abstract
The stereocontrolled synthesis of saturated nitrogen-containing heterocycles has continuously been of interest to pharmaceutical companies owing to their known biological activities. One of these N-heterocyclic scaffolds is the [3.3.1] azabicyclic motif, which is resident in piperazine natural products and pharmaceuticals such as Saframycin A. Here, we describe a step-economical, cost-effective, transition metal-free and mild approach to highly functionalized [3.3.1]-bicyclic piperazines bearing at least five stereocenters, three of which are contiguous. The success of the methodology hinges on a cascade reaction triggered by the addition of allyl magnesium bromide to a lactamoyl ester. The [3.3.1] azabicyclic piperazinols are subsequently engaged in structure-activity-relationship (SAR) studies on neglected tropical diseases (NTDs), including leishmaniasis.
Recommended Citation
Moreno, Antonio, "Intramolecular hydroalkylation of in situ-generated bis-homoallylic chiral piperazinonates" (2019). Symposium Of University Research and Creative Expression (SOURCE). 83.
https://digitalcommons.cwu.edu/source/2019/Oralpres/83
Department/Program
Chemistry
Slides for SOURCE 2019 presentation Moreno
Additional Files
Antonio Moreno_SOURCE_2019.pptx (3037 kB)Slides for SOURCE 2019 presentation Moreno
Intramolecular hydroalkylation of in situ-generated bis-homoallylic chiral piperazinonates
Ellensburg
The stereocontrolled synthesis of saturated nitrogen-containing heterocycles has continuously been of interest to pharmaceutical companies owing to their known biological activities. One of these N-heterocyclic scaffolds is the [3.3.1] azabicyclic motif, which is resident in piperazine natural products and pharmaceuticals such as Saframycin A. Here, we describe a step-economical, cost-effective, transition metal-free and mild approach to highly functionalized [3.3.1]-bicyclic piperazines bearing at least five stereocenters, three of which are contiguous. The success of the methodology hinges on a cascade reaction triggered by the addition of allyl magnesium bromide to a lactamoyl ester. The [3.3.1] azabicyclic piperazinols are subsequently engaged in structure-activity-relationship (SAR) studies on neglected tropical diseases (NTDs), including leishmaniasis.
https://digitalcommons.cwu.edu/source/2019/Oralpres/83
Faculty Mentor(s)
Timothy Beng