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You searched for subject:(ketoimine). Showing records 1 – 2 of 2 total matches.

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University of Notre Dame

1. Jeffrey Munson Carney. Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>.

Degree: PhD, Chemistry and Biochemistry, 2009, University of Notre Dame

The intramolecular hydroamination reaction is among the more versatile means of forming nitrogen-containing hetereocycles, compounds of interest in a variety of chemical disciplines. While the reaction has been intensely studied, concerns still exist over its amenability to organic synthesis. This thesis details the implementation of a readily-recyclable silver-1,10-phenanthroline catalyst which has demonstrated high efficiency for the hydroamination of a variety of aminoalkynes. As a means for developing a protocol for enantioselective synthesis, the desymmetrization of a prochiral diyne was accomplished using the silver-1,10-phenanthroline catalyst. This desymmetrization creates chiral compounds, an occurrence not often observed in the alkyne hydroamination. A separate project involved in the development of improved immunotherapies led us to develop and complete a synthesis of β-hydroxy-methionine. The third attempt via vinyl glycine eventually allowed for the completion of this molecule. It is planned for this amino acid derivative to be included in an antigenic peptide. Advisors/Committee Members: Olaf Wiest, Committee Member, Paul Helquist, Committee Chair, Marya Lieberman, Committee Member, Brian Baker, Committee Member.

Subjects/Keywords: hydroamination; transition metal catalysis; synthesis; unnatural amino acid; ketoimine; prochiral aminodiyne

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Carney, J. M. (2009). Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>. (Doctoral Dissertation). University of Notre Dame. Retrieved from https://curate.nd.edu/show/dj52w378667

Chicago Manual of Style (16th Edition):

Carney, Jeffrey Munson. “Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>.” 2009. Doctoral Dissertation, University of Notre Dame. Accessed June 20, 2019. https://curate.nd.edu/show/dj52w378667.

MLA Handbook (7th Edition):

Carney, Jeffrey Munson. “Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>.” 2009. Web. 20 Jun 2019.

Vancouver:

Carney JM. Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>. [Internet] [Doctoral dissertation]. University of Notre Dame; 2009. [cited 2019 Jun 20]. Available from: https://curate.nd.edu/show/dj52w378667.

Council of Science Editors:

Carney JM. Intramolecular Hydroamination of Alkynes Catalyzed by Silver-Phenanthroline Complexes</h1>. [Doctoral Dissertation]. University of Notre Dame; 2009. Available from: https://curate.nd.edu/show/dj52w378667


Boston College

2. Wieland, Laura Caroline. Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans.

Degree: PhD, Chemistry, 2008, Boston College

Chapter 1: We disclose an Al-catalyzed enantioselective method for additions of Me2Zn and Et2Zn to α-ketoesters bearing aromatic alkenyl, and alkyl substituents. These transformations are promoted in the presence of a readily available amino acid-based ligand, and afforded the desired products in excellent yields and in up to 95% ee. In addition, we discovered a remarkable enhancement of efficiency and selectivity in the presence of an achiral phosphoramidate additive. Chapter 2: An efficient diastereo- and enantioselective Ag-catalyzed method for additions of a commercially available siloxyfuran to α-ketoimine esters is disclosed. Catalytic transformations require an inexpensive metal salt (AgOAc) and an air stable chiral ligand that is readily prepared in three steps from commercially available materials in 42% overall yield. Aryl- as well as heterocyclic substituted ketoimines can be used effectively in the Ag-catalyzed process. Additionally, two examples regarding reactions of alkyl-substituted ketoimines are presented. An electronically modified N-aryl group is introduced that is responsible for high reaction efficiency (>98% conversion, 72–95% yields after purification), diastereo- (up to >98:2 dr) and enantioselectivity (up to 97:3 er or 94% ee). The new N-aryl unit is also crucial for conversion of the asymmetric vinylogous Mannich products to the unprotected amines in high yields. Spectroscopic and X-ray data are among the physical evidence provided that shed light on the identity of the Ag-based chiral catalysts and some of the mechanistic subtleties of this class of enantioselective C–C bond forming processes. Advisors/Committee Members: Amir H. Hoveyda (Thesis advisor).

Subjects/Keywords: catalytic; enantioselective; Mannich; tertiary alcohol; ketoimine

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Wieland, L. C. (2008). Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:101833

Chicago Manual of Style (16th Edition):

Wieland, Laura Caroline. “Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans.” 2008. Doctoral Dissertation, Boston College. Accessed June 20, 2019. http://dlib.bc.edu/islandora/object/bc-ir:101833.

MLA Handbook (7th Edition):

Wieland, Laura Caroline. “Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans.” 2008. Web. 20 Jun 2019.

Vancouver:

Wieland LC. Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans. [Internet] [Doctoral dissertation]. Boston College; 2008. [cited 2019 Jun 20]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101833.

Council of Science Editors:

Wieland LC. Catalytic enantioselective synthesis of O- and N-substituted quaternary carbon stereogenic centers : 1. AL-catalyzed alkylations of α-ketoesters with dialkylzinc reagents. 2. AG-catalyzed vinylogous Mannich-type reactions of α-ketoimine esters with siloxyfurans. [Doctoral Dissertation]. Boston College; 2008. Available from: http://dlib.bc.edu/islandora/object/bc-ir:101833

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