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The Synthesis and Applications of Sulfoxide Ligands and Methodology Development Towards Β-Amino Acid Incorporation in Peptides

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The Synthesis and Applications of Sulfoxide Ligands and Methodology Development Towards Β-Amino Acid Incorporation in Peptides The Synthesis and Applications of Sulfoxide Ligands and Methodology Development Towards β-Amino Acid Incorporation in Peptides by Priscilla Leung A thesis submitted in conformity with the requirements for the degree of Masters of Science Department of Chemistry University of Toronto © Copyright by Priscilla Leung 2011 The Synthesis and Applications of Sulfoxide Ligands and Methodology Development Towards β-Amino Acid Incorporation in Peptides Priscilla Leung Masters of Science Department of Chemistry University of Toronto 2011 Abstract 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 β-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 β-amino acids will be proposed. Lastly, a hydroamidation-type strategy for the construction of β3-amino acids, or more specifically of β-(N-acylamino)acrylates, will be presented as preliminary work towards the goal of dipeptide synthesis. ii Acknowledgments First and foremost, I would like to thank Prof. Vy Dong for all her support and guidance throughout the past year. Thank you for your inspiration, passion for science, and for all the hard work you put in for your students. Thank you to Peter Dornan for initiating the sulfoxide project and sharing his great ideas with me during our collaboration. Thank you to Hasan Khan and Boni Kim for always being there to talk about peptides. Thank you to Wilmer Alkhas for all his hard work, stories and jokes, and for being there to always lighten the mood. I also want to specially thank Tom Hsieh for continuously lending me a helping hand – you are a great chemist, mentor and friend. Thank you to the entire Dong group, who together make the lab a better place and one of the most positive and fun working environments I have ever been in. Lastly, I would like to acknowledge all my family and friends who have forever believed in me and encouraged me to reach for the stars. iii Table of Contents Acknowledgments .......................................................................................................................... iii Table of Contents ........................................................................................................................... iii List of Abbreviations .................................................................................................................... vii List of Tables ................................................................................................................................ xii List of Schemes ............................................................................................................................ xiii List of Figures .............................................................................................................................. xiv List of Appendices ........................................................................................................................ xv Chapter 1 Synthesis and Applications of Novel C3- and C2-Symmetric Sulfoxide Ligands .......... 1 1.1 Introduction ......................................................................................................................... 1 1.1.1 Recent Sulfoxide Ligands in Catalysis ................................................................... 1 1.1.2 Sulfoxides versus Phosphines ................................................................................. 2 1.1.3 Could Sulfoxide Ligands Solve Problems in Hydroacylation? .............................. 3 1.1.4 Applications of C3-Symmetry ................................................................................. 4 1.1.5 The Horeau Principle .............................................................................................. 5 1.2 Research Goals .................................................................................................................... 6 1.3 Results and Discussion ....................................................................................................... 6 1.3.1 C3-Symmetric Ligand Synthesis ............................................................................. 6 1.3.1.1 Application to Asymmetric 1,4-Addition Reactions ................................ 8 1.3.2 C2-Symmetric Ligands .......................................................................................... 11 1.3.2.1 Application to Asymmetric 1,4-Addition Reactions .............................. 12 1.3.3 Conclusions and Future Work .............................................................................. 13 1.3.4 Experimental Procedures ...................................................................................... 14 1.3.4.1 General Considerations........................................................................... 14 1.3.4.2 General Procedure for Trisulfides .......................................................... 15 iv 1.3.4.3 General Procedure for Racemic Oxidation ............................................. 15 1.3.4.4 General Procedure for Asymmetric Oxidation ....................................... 15 1.3.4.5 General Procedure for Rhodium Catalyzed 1,4-Additions ..................... 16 1.3.4.6 Characterization Data ............................................................................. 16 Chapter 2 Peptides by a Novel Condensation and Reduction Strategy ........................................ 19 2.1 Introduction ....................................................................................................................... 19 2.1.1 Importance of -Peptides ...................................................................................... 19 2.1.2 Traditional Methods for Peptide Synthesis and Their Applicability to - Peptide Synthesis .................................................................................................. 20 2.1.3 Iterative Strategy for -Peptide Synthesis ............................................................ 22 2.2 Research Goals .................................................................................................................. 23 2.3 Results and Discussion ..................................................................................................... 24 2.3.1 One Protecting Group ........................................................................................... 24 2.3.2 Aminolysis of Starter Residue .............................................................................. 25 2.3.3 Condensation ......................................................................................................... 26 2.3.4 Reduction – A Catalyst-Controlled Hydrogenation .............................................. 27 2.3.5 Challenges of Aminolysis of a Dipeptide ............................................................. 28 2.3.5.1 N-Methylation ......................................................................................... 29 2.3.5.2 Thiol-Promoted Aminolysis ................................................................... 30 2.3.6 Preliminary Attempts of a Second Condensation en route to a Tripeptide ........... 31 2 2.3.7 Preliminary Model Study for -Amino Acid Incorporation ................................ 31 2.4 Conclusions and Future Work .......................................................................................... 32 2.5 Experimental Procedures and Characterization Data ....................................................... 32 2.5.1 First Aminolysis .................................................................................................... 32 2.5.2 General Procedure for Condensation .................................................................... 33 2.5.3 General Procedure for Asymmetric Hydrogenation ............................................. 34 v 2.5.4 General Procedure for Hydrogenations With an Achiral Catalyst ........................ 35 2.5.5 General Procedure for Dipeptide Aminolysis ...................................................... 36 2.5.6 Tripeptide .............................................................................................................. 37 2.5.7 β2-Test Substrates.................................................................................................. 37 Chapter 3 Synthesis of (Z)-β-(N-acylamino)acrylates: Progress Towards Dipeptide Synthesis via a Hydroamidation-Type Disconnection Strategy ............................................................... 39 3.1 Introduction and Research Goals ...................................................................................... 39 3.2 Results and Discussion ..................................................................................................... 40 3.2.1 Initial Screenings .................................................................................................. 40 3.2.2 Exploring Gold Catalysis ...................................................................................... 43 3.2.3 Adaptions from Other Literature Precedents ........................................................ 45 3.2.4
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