Presentation Title

Intramolecular Hydroamination of Alkenes using organocatalysts

Faculty Mentor

Anna Wenzel

Start Date

23-11-2019 8:00 AM

End Date

23-11-2019 8:45 AM

Location

261

Session

poster 1

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Hydroamination reactions are a favored approach for the creation of chiral amines, which have proven utility to the pharmaceutical industry. These reactions are ideal due to their atom economic and green characteristics. To date, many reported hydroamination reactions are catalyzed by metals, a majority of which are endangered due to overuse. Metal catalysts can also be difficult to completely remove from reaction products. Herein, we explore the use of ammonium salts as an organocatalytic alternative for the intramolecular hydroamination of alkenes to afford pyrrolidine-based products. Preliminary work has demonstrated that this reaction can readily occur in tetrachloroethane using ammonium trifluoroacetate (10 mol%) as the reaction catalyst. Building off of this lead result, asymmetric induction via the use of chiral ammonium salts is currently being explored; the results of these studies are discussed herein.

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Nov 23rd, 8:00 AM Nov 23rd, 8:45 AM

Intramolecular Hydroamination of Alkenes using organocatalysts

261

Hydroamination reactions are a favored approach for the creation of chiral amines, which have proven utility to the pharmaceutical industry. These reactions are ideal due to their atom economic and green characteristics. To date, many reported hydroamination reactions are catalyzed by metals, a majority of which are endangered due to overuse. Metal catalysts can also be difficult to completely remove from reaction products. Herein, we explore the use of ammonium salts as an organocatalytic alternative for the intramolecular hydroamination of alkenes to afford pyrrolidine-based products. Preliminary work has demonstrated that this reaction can readily occur in tetrachloroethane using ammonium trifluoroacetate (10 mol%) as the reaction catalyst. Building off of this lead result, asymmetric induction via the use of chiral ammonium salts is currently being explored; the results of these studies are discussed herein.