Synthesis of amino- and hydroxyl-substituted bridged bicyclic compounds and their application in asymmetric catalysis

Cecilia Olsson

Research output: ThesisDoctoral Thesis (compilation)

Abstract

In this work, hydroxyl- and amino-substituted bridged bicyclic compounds based on bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane and bicyclo[3.3.1]nonane were synthesized and investigated for use in asymmetric catalysis.

An improved process for the preparation of an optically active key intermediate for the synthesis of bicyclo[2.2.2]octane-derivatives, using genetically engineered yeast, was developed. Optically active key intermediates for the synthesis of bicyclo[2.2.1]heptane-derivatives were achieved by enzymatic resolution using Novozym 435. The possibility to use genetically engineered yeast strains for kinetic resolution of a bicyclic epoxyketone was also investigated. The structurally rigid aminoalcohols and diols based on bicyclo[2.2.1]heptane and bicyclo[2.2.2]octane were tested as catalysts in the diethylzinc addition to benzaldehyde.

Chiral cleft-shaped molecules based on dibenzobicyclo[3.3.1]nonane were synthesized and applied as hydrogen-bonding organocatalysts in an asymmetric hetero-Diels-Alder reaction.
Original languageEnglish
QualificationDoctor
Awarding Institution
  • Centre for Analysis and Synthesis
Supervisors/Advisors
  • Frejd, Torbjörn, Supervisor
Award date2008 May 23
ISBN (Print)978-91-7422-196-1
Publication statusPublished - 2008

Bibliographical note

Defence details

Date: 2008-05-23
Time: 09:30
Place: Kemicentrum, Hörsal K:C

External reviewer(s)

Name: Olofsson, Berit
Title: Senior lecturer
Affiliation: Stockholm University

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The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry

Free keywords

  • organocatalysis
  • asymmetric catalysis
  • bicyclo[2.2.1]heptane
  • bicyclo[2.2.2]octane
  • dibenzobicyclo[3.3.1]nonane
  • bioreduction
  • enzymatic kinetic resolution

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