Abstract

In this document we report the synthesis, characterization, and utility of a chiral amidoacrylate substrate. This substrate features a reactive alkene that can be used in a variety of reactions. [3+2]-Cycloaddition reactions to form pyrroloindolines are shown to proceed with excellent diastereoselectivity (>20:1) and yield (86%). [3+2]-Reactions allow for the stereoselective construction of the pyrroloindoline backbone common in many natural products. Diels-Alder reactions catalyzed by TiCl4 show high yields (82%) with ~2:1 diastereoselectivity. Cyclopropanation reactions proceed in moderate yield (71%) and diastereoselectivity (~3:1). Both Diels-Alder and cyclopropanation reactions utilizing the chiral amidoacrylate substrate serve to stereoselectively produce unnatural amino acids which can serve as building blocks for natural products or aid in peptide stabilization. Further chiral Lewis acid catalyzed studies using an achiral amidoacrylate substrate are also explored.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

https://lib.byu.edu/about/copyright/

Date Submitted

2021-07-27

Document Type

Dissertation

Handle

http://hdl.lib.byu.edu/1877/etd12514

Keywords

Acetamide, amidoacrylate, Diels-Alder, Cyclopropanation, Cycloaddition, Evans auxiliary

Language

english

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