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

Research output: ThesisDoctoral Thesis (compilation)

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 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.

Details

Authors
Organisations
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry

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
Original languageEnglish
QualificationDoctor
Awarding Institution
Supervisors/Assistant supervisor
Thesis sponsors
  • Lund University
Award date2019 Sep 20
Place of PublicationLund
Publisher
  • Printed in Sweden by Media-Tryck, Lund University
Print ISBNs978-91-7422-675-1
Electronic ISBNs978-91-7422-676-8
Publication statusPublished - 2019 Aug 27
Publication categoryResearch

Bibliographic note

Defence details Date: 2019-09-20 Time: 09:00 Place: Lecture Hall C, Kemicentrum, Naturvetarvägen 14, Lund External reviewer(s) Name: Pihko, Petri Title: Professor Affiliation: University of Jyväskylä, Finland ---

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