Synthesis of N-Containing Compounds: Development of Methodology and its Application in Total Synthesis
(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:
https://lup.lub.lu.se/record/ccc46933-80cd-4cd5-bbe5-d41fd9b020d6
- author
- Yu, Lu LU
- supervisor
-
- Peter Somfai LU
- Daniel Strand LU
- opponent
-
- Professor Pihko, Petri, University of Jyväskylä, Finland
- organization
- publishing date
- 2019-08-27
- 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
- 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
- 2023-09-07 09:15:58
@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}}, 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}}, language = {{eng}}, month = {{08}}, publisher = {{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/files/68717854/Lu_Yu_without_papers.pdf}}, year = {{2019}}, }