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Synthesis of N-Containing Compounds: Development of Methodology and its Application in Total Synthesis

Yu, Lu LU (2019)
Abstract
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.
Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.
Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.
Chapter 4... (More)
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.
Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.
Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.
Chapter 4 describes an asymmetric formal hydroamination of enamines approach using Cu-H catalyst for the synthesis of chiral 1,2-diamines. The method provides a straightforward method for the synthesis of chiral 1,2-dialkyl amines in good yields with high level of enantioselectivities for a broad range of substrates and should
have significant value for the preparation of molecules bearing a 1,2-diamine motif. (Less)
Abstract (Swedish)
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.
Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.
Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.
Chapter 4... (More)
This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.
Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.
Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.
Chapter 4 describes an asymmetric formal hydroamination of enamines approach using Cu-H catalyst for the synthesis of chiral 1,2-diamines. The method provides a straightforward method for the synthesis of chiral 1,2-dialkyl amines in good yields with high level of enantioselectivities for a broad range of substrates and should
have significant value for the preparation of molecules bearing a 1,2-diamine motif. (Less)
Please use this url to cite or link to this publication:
author
supervisor
opponent
  • Professor Pihko, Petri, University of Jyväskylä, Finland
organization
publishing date
type
Thesis
publication status
published
subject
keywords
a-keto amides, enamine catalysis, pyrrolidine, TEMPO, a-keto thioamides, a-keto amidines, a-amino-b-hydroxy ester, asymmetric transfer hydrogenation, alexine, dynamic kinetic resolution, hydroamination, 1,2-diamines, enamines, copper
pages
142 pages
publisher
Printed in Sweden by Media-Tryck, Lund University
defense location
Lecture Hall C, Kemicentrum, Naturvetarvägen 14, Lund
defense date
2019-09-20 09:00:00
ISBN
978-91-7422-676-8
978-91-7422-675-1
language
English
LU publication?
yes
id
ccc46933-80cd-4cd5-bbe5-d41fd9b020d6
date added to LUP
2019-08-21 17:46:32
date last changed
2019-08-27 16:02:16
@phdthesis{ccc46933-80cd-4cd5-bbe5-d41fd9b020d6,
  abstract     = {This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.<br/>Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.<br/>Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.<br/>Chapter 4 describes an asymmetric formal hydroamination of enamines approach using Cu-H catalyst for the synthesis of chiral 1,2-diamines. The method provides a straightforward method for the synthesis of chiral 1,2-dialkyl amines in good yields with high level of enantioselectivities for a broad range of substrates and should<br/>have significant value for the preparation of molecules bearing a 1,2-diamine motif.},
  author       = {Yu, Lu},
  isbn         = {978-91-7422-676-8},
  language     = {eng},
  month        = {08},
  publisher    = {Printed in Sweden by Media-Tryck, Lund University},
  school       = {Lund University},
  title        = {Synthesis of N-Containing Compounds: Development of Methodology and its Application in Total Synthesis},
  url          = {https://lup.lub.lu.se/search/ws/files/68661221/Lu_Yu_complete_file.pdf},
  year         = {2019},
}