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.
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 language | English |
---|---|
Qualification | Doctor |
Awarding Institution |
|
Supervisors/Advisors |
|
Award date | 2008 May 23 |
ISBN (Print) | 978-91-7422-196-1 |
Publication status | Published - 2008 |
Bibliographical note
Defence detailsDate: 2008-05-23
Time: 09:30
Place: Kemicentrum, Hörsal K:C
External reviewer(s)
Name: Olofsson, Berit
Title: Senior lecturer
Affiliation: Stockholm University
---
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