Degree Type
Honors Capstone Project
Date of Submission
Spring 5-2017
Capstone Advisor
Nancy Totah
Honors Reader
Michael Sponsler
Capstone Major
Chemistry
Capstone College
Arts and Science
Audio/Visual Component
no
Capstone Prize Winner
no
Won Capstone Funding
yes
Honors Categories
Sciences and Engineering
Subject Categories
Chemistry
Abstract
The purpose of this research is to explore the use of cobalt- and iron-catalyzed cross coupling reactions of alkyl iodides containing beta-tetrahydropyran groups to develop a general method to synthesize substituted tetrahydropyrans. Substituted tetrahydropyrans can be used towards the total syntheses of biologically active natural products. The starting iodide compounds underwent sp3-sp3 and sp3-sp2 cobalt- and iron-catalyzed cross-coupling reactions with different Grignard reagents. It was expected that the formation of the coupled product would be faster than the formation of the side products (elimination and homocoupling) and thus yield the desired substituted tetrahydropyrans. The results of this study showed that cobalt-catalyzed reactions are best used for sp3-sp3 coupling though in low yields while the iron-catalyzed reactions produced better yields for the sp3-sp2 couplings. However, the reactions still resulted in the formation of undesired elimination and homocoupling side products. In the future, optimization will be made to minimize the formation of the side products and to increase yields of the substituted tetrahydropyrans which can then provide a further basis for the use of cobalt- and iron-catalyzed cross-coupling reactions in the synthesis of natural products.
Recommended Citation
Lieu, Amanda, "Synthesis of substituted tetrahydropyrans using metal-catalyzed coupling reaction" (2017). Honors Capstone Projects - All. 1040.
https://surface.syr.edu/honors_capstone/1040
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
