ORCID Identifier(s)

0009-00068286-3724

Graduation Semester and Year

Spring 2024

Language

English

Document Type

Thesis

Degree Name

Master of Science in Chemistry

Department

Chemistry and Biochemistry

First Advisor

Junha Jeon

Abstract

Reduction of esters to aldehydes poses a challenge since the resulting aldehydes are often more reactive than the initial esters toward nucleophilic hydride-reducing agents. Although bulky, more controllable reducing agents such as lithium tri-tert-butoxyaluminum hydride or diisobutylaluminum hydride (DIBAL-H) have been developed, they are hazardous, sensitive to moisture and air, needing strict reaction conditions, and unsuitable with a wide range of functional groups. We present the design of an iridium-catalyzed chemoselective hydrosilylation method for dicarboxylic imides, followed by hydrolysis to eliminate the amide and yield aldehydes. This approach offers versatility in general reduction chemistry, holds promise for application in asymmetric synthesis, and facilitates straightforward removal of Evans-type chiral auxiliaries.

Disciplines

Organic Chemistry

License

Creative Commons Attribution 4.0 International License
This work is licensed under a Creative Commons Attribution 4.0 International License.

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