Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands

Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands

Bibliographic Details
Main Author: Lineberry, Aaron M.
Language:English
Published: University of Akron / OhioLINK 2011
Subjects:
Chemistry
Thia-Aza ligands
Microwave-Assisted
Organic Synthesis
Mixed-Donor
3-pyrroline
Online Access:http://rave.ohiolink.edu/etdc/view?acc_num=akron1310944928
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spelling ndltd-OhioLink-oai-etd.ohiolink.edu-akron13109449282021-08-03T05:26:32Z Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands Lineberry, Aaron M. Chemistry Thia-Aza ligands Microwave-Assisted Organic Synthesis Mixed-Donor 3-pyrroline Given the continued interest in the use of enantioselective metal-catalyzed asymmetric reactions in organic synthesis, there have been considerable research efforts in the development of new chiral ligands consisting of mixed-donor heteroatoms. This dissertation involves the microwave-assisted synthesis of amino acid-derived pyrrolidine thioethers, as well as a thiolane-based analogue consisting of meso frameworks as opposed to the conventional C2 symmetry found in most chiral ligands. Chapter I of this work gives a brief literature review in the synthesis and applications of pyrrolidine-based ligand systems. Also discussed is a review of 3-pyrroline derivatives, which are an important class of heterocycles used as precursors in the synthesis of 3,4-disubstituted pyrrolidines, as well as several synthetic approaches towards their preparation. Chapter II of this work describes the microwave-assisted synthesis of a series of chiral amino acid-derived pyrrolidine diols, from the appropriate L-amino acid methyl ester hydrochlorides (Leu, Val, Phe) or benzyl esters (Gly, Ala, Ser) and cis-1,4-dichloro-2-butene. The enantiopurity of the chiral 3-pyrroline intermediates have been established through Mosher ester synthesis and by comparison of optical rotation of the amino acid esters. Also, the attempted conversion of the diols into thioethers is discussed. The multi-step synthesis of thiolane analogues, as well as approaches towards novel heterobicyclo[4.3.0]nonanes is discussed. Finally, a modified approach towards the tripodal ligand system [9]aneN2S and a microwave-assisted cyclization of [9]aneN3 are discussed. 2011-08-03 English text University of Akron / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=akron1310944928 http://rave.ohiolink.edu/etdc/view?acc_num=akron1310944928 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws.
collection NDLTD
language English
sources NDLTD
topic Chemistry
Thia-Aza ligands
Microwave-Assisted
Organic Synthesis
Mixed-Donor
3-pyrroline
spellingShingle Chemistry
Thia-Aza ligands
Microwave-Assisted
Organic Synthesis
Mixed-Donor
3-pyrroline
Lineberry, Aaron M.
Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
author Lineberry, Aaron M.
author_facet Lineberry, Aaron M.
author_sort Lineberry, Aaron M.
title Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
title_short Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
title_full Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
title_fullStr Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
title_full_unstemmed Microwave-Assisted Synthesis of Small Ring Thia-Aza Mixed-Donor Ligands
title_sort microwave-assisted synthesis of small ring thia-aza mixed-donor ligands
publisher University of Akron / OhioLINK
publishDate 2011
url http://rave.ohiolink.edu/etdc/view?acc_num=akron1310944928
work_keys_str_mv AT lineberryaaronm microwaveassistedsynthesisofsmallringthiaazamixeddonorligands
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