Date of Award

1-1-2018

Document Type

Dissertation

Degree Name

Ph.D.

Department

Chemistry and Biochemistry

First Advisor

Bryan J. Cowen, Ph.D.

Keywords

Aldol reactions, Brønsted acid catalysis, Carbon-carbon bond forming, Diastereoselectivity, Sulfonic acids

Abstract

The focus of this research project lies in the development of new methodology in the field of Brønsted acid catalysis enabling rapid synthesis of medicinally relevant compounds. It is foreseen that small molecule sulfonic acids evaluated in this research project will unveil new asymmetric carbon carbon bond forming reactions between substrates hitherto unexplored with Brønsted acid catalysis. It has been established that strong Brønsted acids, such as phosphoric acids, are capable of mediating highly selective transformations operating through unique mechanistic manifolds.

Specific focus for the sulfonic acid catalysts was geared towards asymmetric coupling reactions with synthetically useful precursors such as azlactones. We have discovered a novel coupling reaction between azlactones and acetals with Brønsted acid catalysis, with simple and universal purification procedure, pure products were isolated with some diastereoselectivities.

The implementation of Newman-Kwart rearrangement afforded desired mono-protic BINOL based sulfonic acid was successfully performed. This will be followed by evaluating sulfonic acid catalytic efficiencies towards asymmetric coupling reactions.

The total synthesis of latifolian A through application of a chiral sulfonic acid catalyzed Friedel–Crafts cyclization reaction as a key synthetic step was designed. This is an ongoing investigation but is promising in the new treatment of Alzheimer's that have potential benefits in medicinal chemistry.

Provenance

Received from ProQuest

Rights holder

Jiangyue Miao

File size

152 p.

File format

application/pdf

Language

en

Discipline

Chemistry, Organic chemistry

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