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Design and evaluation of a new Lewis acid-assisted Lewis acid catalyst system and further applications of a double-allylation reagent Open Access

Descriptions

Other title
Subject/Keyword
Asymmetric synthesis
Catalysis
Lewis acids
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Sivasubramaniam, Umakanthan
Supervisor and department
Prof. Dennis G. Hall (Department of Chemistry)
Examining committee member and department
Prof. Rik R. Tykwinski (Department of Chemistry)
Prof. Andreas Schieber (Department of Agricultural, Food, and Nutritional Sciences)
Department
Department of Chemistry
Specialization

Date accepted
2009-10-02T21:31:28Z
Graduation date
2009-11
Degree
Master of Science
Degree level
Master's
Abstract
Asymmetric synthesis is one of the most important areas of organic chemistry. Despite of the prevalence of asymmetric catalysts, there is still room for improved catalyst systems. Chapter 2 describes the design and evaluation of a new Lewis acid-assisted Lewis acid (LLA) catalyst system. Many boronic esters were prepared for this purpose and combined with different Lewis acids to form LLA catalyst systems. These LLA species were examined in carbonyl allylation reactions. In a few cases, higher product conversions were observed with the new LLA catalyst systems compared to the corresponding background reactions (Lewis acid alone). A novel class of chiral double-allylation reagent 7 was recently introduced by our group. Hall and Peng showed the stereoselective synthesis of trisubstituted furans, vinylcyclopropanes, and smaller oxabicyclic compounds using this double allylation reagent. Chapter 3 describes further applications of double allylation reagent 7. In this chapter, the synthesis of larger oxabicyclic compounds, a one-pot synthesis of furan rings, and the synthesis of pyrrolidines were examined. From the preliminary studies, it was observed that the synthesis of pyrrolidines may be feasible. Moreover, trisubstituted tetrahydrofurans 46_49 were prepared in a one-pot protocol with excellent diastereoselectivities (≥20:1).
Language
English
DOI
doi:10.7939/R37H2Z
Rights
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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