Benjamin H. Shupe
- Courses2
- Reviews3
- School: California State University
- Campus: Sacramento
- Department: Chemistry
- Email address: Join to see
- Phone: Join to see
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Location:
6000 J Street
Sacramento, CA - 95819 - Dates at California State University: February 2018 - May 2018
- Office Hours: Join to see
Biography
Benjamin H Shupe is a/an Lecturer in the California State University department at California State University
California State University Sacramento - Chemistry
Product and Curriculum Developer at Hands-On Labs (HOL)
Higher Education
Ben
Shupe
Fort Collins, Colorado
I have a PhD in organic chemistry from the University of California, Davis that I earned 2015. I performed research under the advisement of Professor Annaliese Franz. My Ph.D. dissertation focused on the development on new synthetic organic reactions, specifically in stereoselective allylsilane annulation reactions to access enantioenriched spirocyclic oxindoles and other heterocycles. I have previously worked as a researcher scientist for Nano Syn Inc. making drug intermediates for our clients. I have experience teaching as an adjunct professor at both Sacramento State and Napa Valley College. At those universities I taught in the areas of organic chemistry, general chemistry and biochemistry. I have experience in as both a lecturer and as a lab instructor. I am currently a product developer for Hands On Labs creating content to support our cloud based platform.
Experience
UC Davis
Doctoral Researcher
Developing and understanding new stereoselective organic transformations using Lewis Acid catalysts and Organocatalysts for the synthesis of 3-aminooxindoles and nitrogen containing spirocyclic oxindoles with application in medicinal chemistry and chemical biology.
• Employed chromatographic and spectroscopic techniques to purify and characterize small organic
molecules
• Used, maintained and trouble shot Agilent Q-TRAP LC/MS/MS System and Shimadzu HPLC
• Optimized reaction conditions lead to the development of new organic reactions
• Published reaction methodology in peer-reviewed journals
• Strong synthetic organic problem solving skills
• Maintained a laboratory notebook detailing experimental procedures, summarized and interpreted data
• Trained and mentored incoming graduate and undergraduate students
• Worked on modules with Allan Doyle to become the 1st Green Lab Certified by University of
California, Davis; Water Module LeaderNapa Valley College
Adjunct Professor
Instructor of record and Laboratory Instructor for Chem 111: Intro to Organic and Biochemistry.
Design lecture and lab material to help student understand the basic principle of organic chemistry and how functional groups can have an effect on biological systems.
Supervise student in a teaching lab.
Create worksheets, handouts and exams based on class material.Nanosyn Inc
Research Scientist
Plan and execute organic reactions on milligram to multi-gram scale
Isolate small molecule targets containing complex heterocyclic cores and purify target molecules using
Combi-Flash silica gel chromatography.
Preform multistep synthesis and analyze reactions by LCMS and 1H NMR
Present data to clients in weekly meeting using PowerPoint
Summarize procedures with reaction schemes as a final report upon completion of a project
Research literature procedures for current projects
Complete projects for client within agreed upon deadlineCalifornia State University-Sacramento
Adjunct Professor
Instructor of record for Chemistry 20: Organic Chemistry Lecture.
Laboratory Instructor for Chemistry 6A and B: Introduction to Organic and Biological Chemistry, Chemistry 25 Organic Chemistry Laboratory.
Plan lecture material for entire semester including writing and grading quiz and exams.
Host office hours to help student with class material.
Supervised undergraduates in a teaching laboratory while helping student troubleshoot the experiments.
Explain to students and follow through on the safety policy’s of the university while in a chemistry lab.Hands-On Labs (HOL)
Product and Curriculum Developer
Write and edit microscale teaching experiments for student taking online science classes, including background content, procedures and premium questions.
Provide customer support to the sales team.
Communicate with the Board of Advisors on improving existing experiments and creating new lessons
Manage various projects to bring new labs and content to our cloud based learning management system.
Peer review internal content before it is published on the cloud.
Part take in webinars focused on HOL's content and learning platform.
Successfully brought labs and content specifically focused on General, Organic and Biochemistry (GOB Chemistry) to the market for distance learning students.
Review and approve physical materials for use in chemistry kits.
Review scientific products aimed at grades K-12 with their product manuals and make suggestions for how to improve both the design and content.
Education
University of Vermont
Bachelor of Science (B.S.)
Chemistry
IES Vienna
Study Abroad Program
German, Vienna History, Philosophy and Sociology
Spring semester study abroad program located in Vienna, Austria.University of California, Davis
Doctor of Philosophy (Ph.D.)
Chemistry
Publications
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles
Chemical Communications
A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters. The addition of NaBArF significantly enhances reactivity, allowing either metal salts or acidic clay to be effective catalysts for the stereoselective reaction.
Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles
Chemical Communications
A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters. The addition of NaBArF significantly enhances reactivity, allowing either metal salts or acidic clay to be effective catalysts for the stereoselective reaction.
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Enantioselective Pictet–Spengler reactions of isatins for the synthesis of spiroindolones
Tetrahedron Letters
The condensation cyclization between isatins and 5-methoxy tryptamine catalyzed by chiral phosphoric acids provides spirooxindole tetrahydro-B-carboline products in excellent yields (up to 99%) and enantioselectivity (up to 98:2 er). A comparison of catalysts provides insight for the substrate scope and factors responsible for efficient catalytic activity and selectivity in the spirocyclization. Chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration.
Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles
Chemical Communications
A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters. The addition of NaBArF significantly enhances reactivity, allowing either metal salts or acidic clay to be effective catalysts for the stereoselective reaction.
Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles
Chemical Communications
A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters. The addition of NaBArF significantly enhances reactivity, allowing either metal salts or acidic clay to be effective catalysts for the stereoselective reaction.
Synthesis of Spirocarbamate Oxindoles via Intramolecular Trapping of B-Silyl Carbocation by and N-Boc Group
Organic Letters
We report the Lewis acid catalyzed additions of allylsilanes to N-Boc-iminooxindoles and the formation of novel silicon-containing spirocarbamates via intramolecular trapping of a β-silyl carbocation by an N-Boc group. Several transformations display the synthetic utility of these spirocarbamate oxindoles, including a reductive cyclization to access new silylated furoindoline derivatives.
Synthesis of Spirocarbamate Oxindoles via Intramolecular Trapping of B-Silyl Carbocation by and N-Boc Group
Organic Letters
We report the Lewis acid catalyzed additions of allylsilanes to N-Boc-iminooxindoles and the formation of novel silicon-containing spirocarbamates via intramolecular trapping of a β-silyl carbocation by an N-Boc group. Several transformations display the synthetic utility of these spirocarbamate oxindoles, including a reductive cyclization to access new silylated furoindoline derivatives.
