Title

Evaluation of cis-diamino-cyclohexane derivatives as potential chiral catalysts in enantioselective organic synthesis

Poster Number

12C

Lead Author Major

Pre-Pharmacy

Lead Author Status

Junior

Format

Poster Presentation

Faculty Mentor Name

Vyacheslav V. Samoshin

Faculty Mentor Email

vsamoshin@pacific.edu

Faculty Mentor Department

Chemistry

Graduate Student Mentor Name

Carim Van Beek

Graduate Student Mentor Email

c_vanbeek@pacific.edu

Graduate Student Mentor Department

Chemistry

Abstract/Artist Statement

Abstract

Enantiomers are chiral molecules that are non-identical mirror images of each other—similar to the left and right hand. A pair of enantiomers exhibit indistinguishable physical properties, but contrasting biological properties. For example, the drug(S,S)-(+)-ethambutol can treat Tuberculosis, while (R,R)-(-)-ethambutol can inflict blindness. Therefore, a selective enantiomer production is vital to the preparation of modern efficient drugs.

This research is an introductory step aimed at developing chiral catalysts that selectively synthesize one enantiomeric product instead of the conventional 50/50 mixture of two enantiomers. We chose a cis-1,2-diaminocyclohexane (DACH) scaffold as the catalytic site for selective synthesis. Its two amino-groups were additionally equipped with supplementary attachments. By adding small quantities of the obtained DACH derivatives to appropriate chemical reactions, we established a fundamental starting point for further broader research towards chiral catalysts by demonstrating catalytic activity for the cis-DACH scaffold. The major accomplishments of this project are the design, optimization of synthesis, and preliminary testing of the model DACH-based catalyst.

Artist Statement

“What’s the point of studying organic chemistry?” is a familiar phrase heard in the pre-pharmacy community. People tend to think it’s a gruesome subject that “inflicts more headaches than smelling ammonia” (as some students might say). However, I developed a passion for organic chemistry and thus, pursued research. I was motivated by my intrinsic fascination with the subject, which was further enhanced when I realized its pharmaceutical significance. The potential to create a catalyst that can selectively synthesize one enantiomer highlights its importance in the preparation of modern efficient drugs. Thus, the results can prospectively improve the health and well-being of people worldwide—a potential worth appreciating and recognizing.

Location

DeRosa University Center Ballroom

Start Date

27-4-2018 12:30 PM

End Date

27-4-2018 2:30 PM

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Apr 27th, 12:30 PM Apr 27th, 2:30 PM

Evaluation of cis-diamino-cyclohexane derivatives as potential chiral catalysts in enantioselective organic synthesis

DeRosa University Center Ballroom

Abstract

Enantiomers are chiral molecules that are non-identical mirror images of each other—similar to the left and right hand. A pair of enantiomers exhibit indistinguishable physical properties, but contrasting biological properties. For example, the drug(S,S)-(+)-ethambutol can treat Tuberculosis, while (R,R)-(-)-ethambutol can inflict blindness. Therefore, a selective enantiomer production is vital to the preparation of modern efficient drugs.

This research is an introductory step aimed at developing chiral catalysts that selectively synthesize one enantiomeric product instead of the conventional 50/50 mixture of two enantiomers. We chose a cis-1,2-diaminocyclohexane (DACH) scaffold as the catalytic site for selective synthesis. Its two amino-groups were additionally equipped with supplementary attachments. By adding small quantities of the obtained DACH derivatives to appropriate chemical reactions, we established a fundamental starting point for further broader research towards chiral catalysts by demonstrating catalytic activity for the cis-DACH scaffold. The major accomplishments of this project are the design, optimization of synthesis, and preliminary testing of the model DACH-based catalyst.

Artist Statement

“What’s the point of studying organic chemistry?” is a familiar phrase heard in the pre-pharmacy community. People tend to think it’s a gruesome subject that “inflicts more headaches than smelling ammonia” (as some students might say). However, I developed a passion for organic chemistry and thus, pursued research. I was motivated by my intrinsic fascination with the subject, which was further enhanced when I realized its pharmaceutical significance. The potential to create a catalyst that can selectively synthesize one enantiomer highlights its importance in the preparation of modern efficient drugs. Thus, the results can prospectively improve the health and well-being of people worldwide—a potential worth appreciating and recognizing.