1. SUMMARY
Chemistry major aspiring to have a career in academia dedicated to organic synthesis and
methodology research
Worked in Snyder Group, an organic synthesis and methodology research group, since January 2015
Has two years of experience as a teaching assistant for four different classes under three professors
Extensive biology and mathematics background
Proficient in data analysis using linear regression techniques, as well as MestreNova NMR analysis
EDUCATION
Boston University College of Arts and Sciences
Bachelor of Science, Chemistry (Expected May 2017)
Cumulative GPA: 3.83, Deans List
Minor in Mathematics and Biology
Kilachand Honors College
Awards
UROP FROG supplies award Spring 2016
KHC student research supplies funding Spring 2016
UROP Summer research funding Summer 2015
RESEARCH EXPERIENCE
Undergraduate Research Assistant in Snyder Group January 2015 to present
Synthesis of 3,6 Dicarboxylate 1,2,4,5 Tetrazines as Dienes for Inverse Electron Demand Diels-Alder
Project Description: The goal of this project is to synthesize a series of 3,6 disubstituted 1,2,4,5 tetrazines to
test their relative reactivity as the diene in an Inverse Electron Demand Diels Alder pathway. Literature
precedents will be used to synthesize the tetrazines with methyl ester, ketone and alcohol groups substituted at
C-3 and C-6. However, the synthesis of amide substituted tetrazines is a novel procedure that is critical for the
project because of the greater electron withdrawing character of amides, which can significantly lower the
LUMO in the inverse electron demand Diels-Alder reaction. The synthesis of the bisamide tetrazines is crucial
because of their low LUMO as well as their ability to form polymers using various diamines. Preliminary tests
have shown the polymerization potential by reacting a diamine with the precursor to the tetrazine ring
formation. The combination of the Diels-Alder reactivity of the tetrazine and the reactivity of diamines can be
used to form temperature selective polymerization that can be detected by the release of nitrogen as well as the
formation of large solids if the tetrazine is linked to a large molecule by an amine. Another application of the
bisamide tetrazine is that it can be integrated within a nylon polymer in an attempt to functionalize the nylon
by allowing the polymer to perform the Diels-Alder chemistry.
Skills
Gained experience of the multistep synthetic organic chemistry and how to appropriately allocate
resources and starting material in order to generate a library of derivatives
Experience in designing useful derivatives in a library in order to obtain relevant kinetic and LUMO
data to verify previously made calculations
Applied practices to remove water from the water sensitive precursors to prevent significant
hydrolysis and maximize yield
Tyler Casselman tdcasse@bu.edu
(716) 480-4674 870 Beacon Street, Boston, MA 02215
2. Develop an undergraduate mentee by teaching the student how to perform the research I have done in
order to introduce the research process.
Copper Catalyzed Cross Coupling of 1,2,4 Triazines with a thioether substituted at C-3
Project Description: The goal of this project is to create a procedure that effectively cross couples a thioether
substituted at C-3 of a triazine with an aryl ring, vinyl group or terminal alkyne via the cross coupling catalytic
cycle. Previous studies have shown the Suzuki cross coupling can be performed on the desired triazine
utilizing an additional copper catalyst to promote the reductive elimination of the thioether group. The main
objective of the project is to design a procedure for a Heck-like cross coupling to attach a vinylic group that
can be transformed into a vinylic amine. This reaction is critical in a prospective three step synthesis of
aaptamine, which is a natural product found to have high antiretroviral, antifungal and antimicrobial activity.
Preliminary results have shown Suzuki-like cross couplings can be performed using a thioether substituent, but
the Heck-like reaction has not yet been confirmed.
Skills
Gained experience of the iterations and difficulties involved in generating a procedure of an unknown
reaction
Learned how to extensively monitor reaction progress by TLC and crude NMR analysis
Presentations
Copper mediated cross coupling of thioether substituted 1,2,4 triazines October 2015
RESEARCH SKILLS
Analytical Techniques- Characterization by 1
H NMR, 13
C NMR, 2-D NMR, IR and LC/MS techniques
Synthetic Chemistries- Tetrazines, Triazines, Diels-Alder cycloadditions, Acylation, Oxidation, Carbonyl
chemistry, SnAr
Laboratory Techniques- Flash chromatography purification, Distillation, Extraction, Cyclic Voltammetry
TEACHING EXPERIENCE
BU Chemistry Department
Undergraduate Assistant Spring 2016 semester
Principles of Biochemistry- Dr. Didem Vardar-Ulu
Carried out two weekly, ninety minute review sessions that served to instruct up to fifteen students at
a time.
Monitored the student’s homework and answers to lecture questions to discover gaps in their learning
to more effectively supplement the lecture content during review sessions
Graded exams and performed administrative tasks
Laboratory Undergraduate Assistant Fall 2015 semester
Principles of General Chemistry- Dr. Didem Vardar Ulu
Instructed, graded and was responsible for the safety and learning of twenty students in the laboratory
Designed methods with other lab instructors and the coordinator to implemented to increase my
pedagogical technique
Undergraduate Assistant Spring 2015 semester
General and Quantitative Analytical Chemistry- Dr. Pinghua Liu
Held a weekly office hour designed to answer the student’s questions regarding homework problems,
discussion worksheets and exam problems
Responsible for the grading of the weekly discussion quizzes and exams of 125 students
3. Laboratory Undergraduate Assistant Fall 2014 semester
Intensive General and Quantitative Analytical Chemistry- Dr. Binyomin Abrams
Assisted the lab instructors with the teachings and held a weekly office hour session
Graded the lab exams and pre-lab assignments for 35 students