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

Cecilia Olsson

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

Cecilia Olsson

Centre for Analysis and Synthesis

Research output: Thesis › Doctoral 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 language	English
Qualification	Doctor
Awarding Institution	Centre for Analysis and Synthesis
Supervisors/Advisors	Frejd, Torbjörn, Supervisor
Award date	2008 May 23
ISBN (Print)	978-91-7422-196-1
Publication status	Published - 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

---

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

Cite this

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title = "Synthesis of amino- and hydroxyl-substituted bridged bicyclic compounds and their application in asymmetric catalysis",

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.",

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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TY - THES

T1 - Synthesis of amino- and hydroxyl-substituted bridged bicyclic compounds and their application in asymmetric catalysis

AU - Olsson, Cecilia

N1 - 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 --- 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)

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

KW - organocatalysis

KW - asymmetric catalysis

KW - bicyclo[2.2.1]heptane

KW - bicyclo[2.2.2]octane

KW - dibenzobicyclo[3.3.1]nonane

KW - bioreduction

KW - enzymatic kinetic resolution

M3 - Doctoral Thesis (compilation)

SN - 978-91-7422-196-1

ER -

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

Abstract

Bibliographical note

Subject classification (UKÄ)

Free keywords

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