Item – Theses Canada

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OCLC number
1019462567
Link(s) to full text
LAC copy
Author
Leung, Priscilla.
Title
The Synthesis and Applications of Sulfoxide Ligands and Methodology Development Towards beta-Amino Acid Incorporation in Peptides.
Degree
M. Sc. -- University of Toronto, 2011
Publisher
Ottawa : Library and Archives Canada = Bibliothèque et Archives Canada, 2012.
Description
1 online resource
Notes
Includes bibliographical references.
Abstract
<?Pub Inc> The use of sulfoxide ligands for transition metal catalyzed transformations has recently been brought to the forefront in organic chemistry. The synthesis of a series of tri- and disulfoxides will be presented, and their applications investigated. Their use in rhodium catalyzed 1,4-additions of phenylboronic acid to 2-cyclohexen-1-one result in enantioselectivities up to 80%. The incorporation of [beta]-amino acid residues into polypeptides has resulted in new foldamers whose structures and enhanced stability provide interesting opportunities for new biological applications. A novel strategy for an iterative peptide synthesis involving [beta]-amino acids will be proposed. Lastly, a hydroamidation-type strategy for the construction of [beta] 3-amino acids, or more specifically of [beta]-('N'-acylamino)acrylates, will be presented as preliminary work towards the goal of dipeptide synthesis.
ISBN
9780494761724
0494761725