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.

Faculty Mentor(s)

Timothy Beng

Department/Program

Chemistry

Antonio Moreno_SOURCE_2019.pptx (3037 kB)
Slides for SOURCE 2019 presentation Moreno

Additional Files

Antonio Moreno_SOURCE_2019.pptx (3037 kB)
Slides for SOURCE 2019 presentation Moreno

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May 15th, 12:00 AM May 15th, 12:00 AM

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