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MULTICOMPONENT REACTIONS OF ALLENYL AND ALKYNYL BORON
DERIVATIVES WITH AMINES AND ALDEHYDES AND THEIR USE IN THE
SYNTHESIS OF NOVEL MULTIFUNCTIONAL AMINES AND
HETEROCYCLES
by
Fotini Liepouri
A Dissertation Presented to the
FACULTY OF THE GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
May 2007
Copyright 2007 Fotini Liepouri
Object Description
| Title | Multicomponent reactions of allenyl and alkynyl boron derivatives with amines and aldehydes and their use in the synthesis of novel multifunctional amines and heterocycles |
| Author | Liepouri, Fotini |
| Author email | liepouri@usc.edu |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2007-03-07 |
| Date submitted | 2007 |
| Restricted until | Unrestricted |
| Date published | 2007-04-24 |
| Advisor (committee chair) | Petasis, Nicos |
| Advisor (committee member) |
Prakash, Surya Schonthal, Axel |
| Abstract | This dissertation presents our efforts in the field of multicomponent reactions and more specifically in the three-component condensation among amines, carbonyl compounds and organoboron derivatives. This process is referred as Petasis reaction in the literature. This thesis describes new extensions of the Petasis reaction to allenyl and alkynyl boron components.; Chapter one is an introduction to the field of multicomponent reactions. A limited historical review is attempted to the landmarks of this Chemistry which established the main principles and demonstrated the potential of this chemistry in many different fields such as basic academic research, synthetic organic chemistry, medicinal and industrial applications.; Chapter two discusses the general features of the Petasis reaction and all the research previously conducted concerning the process. Furthermore, our initial efforts in expanding the process to new boron components such as allenyl boron derivatives are included. Interesting features for the synthetic potential of the process were reveled through multiple types of reagents-controlled synthesis for the two isomeric types of products that can potentially be obtained (homopropargylic versus allenic scaffolds).; Chapter three discusses the stereoselectivity of the Petasis reaction when chiral components are used in combination with allenyl boronic acid and potassium allenyl trifluoroborate salt. The degree of chiral induction of various chiral amines on the reaction and the determination of the absolute stereochemical preference are discussed. Also, results of the use of chiral alfa-hydroxy aldehydes to control the diastereoselectivity of the allenyl version of the Petasis reaction are presented.; Chapter four concerns our results in developing methodology towards novel alfa and gama- monosubstituted allenyl boron analogues and in exploring their role in the three-component condensation with amines and carbonyl compound. Five novel analogues were synthesized and used in the Petasis reaction yielding a number of novel multifunctionalized amine derivatives.; Chapter five deals with the synthetic manipulation of the allenyl adducts obtained from the Petasis reaction. The reactivity of the allenyl moiety towards palladium promoted transformations allowed for the synthesis of various heterocycles.; Chapter six discusses our efforts in synthesizing a novel alkynyl boron analog and our initial studies of reactivity of this boron source in the Petasis reaction. A number of propargyl amines were synthesized by those attempts where the scope and limitations of this version were revealed. |
| Keyword | multicomponent reactions; MCRs; allenyl amines; homopropargyl amines; propargyl amines; allenyl boronic acid; allenyl boronate; potassium allenyl trifluoroborate; palladium annulation; aziridine |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Type | texts |
| Legacy record ID | usctheses-m436 |
| Rights | Liepouri, Fotini |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Liepouri-20070424 |
| Archival file | uscthesesreloadpub_Volume48/etd-Liepouri-20070424.pdf |
Description
| Title | Page 1 |
| Full text | MULTICOMPONENT REACTIONS OF ALLENYL AND ALKYNYL BORON DERIVATIVES WITH AMINES AND ALDEHYDES AND THEIR USE IN THE SYNTHESIS OF NOVEL MULTIFUNCTIONAL AMINES AND HETEROCYCLES by Fotini Liepouri A Dissertation Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) May 2007 Copyright 2007 Fotini Liepouri |
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