St Andrews Research Repository

St Andrews University Home
View Item 
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  •   St Andrews Research Repository
  • Chemistry (School of)
  • Chemistry
  • Chemistry Theses
  • View Item
  • Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

Synthesis studies to single stereoisomers of the vicinal trifluoroalkane motif

Thumbnail
View/Open
VincentBrunetPhDThesis.pdf (4.276Mb)
Date
2009
Author
Brunet, Vincent A.
Supervisor
O'Hagan, David
Metadata
Show full item record
Abstract
This thesis focuses on the construction of individual isomers of the R-CHF-CHF-CHF-R’ motif. The multi-vicinal fluorine motif is new in organic chemistry and therefore stereoselective methods giving rapid access to these motifs and with flexibility need to be explored. The research in the thesis succeeded in the preparation of (2S,3R,4S)-314 and (2S,3S,4R)-328. In Chapter 1, an overview of the impact of fluorine in organic molecules is given. Recent developments in asymmetric electrophilic and nucleophilic fluorination are described, as well as the preparation of multivicinal fluoroalkane motifs. Aldol reactions of either (R)- or (S)-N-(α-fluoropropyl)-2-oxazolidinones, mediated by TiCl 4 are reported in Chapter 2. Such aldol reactions gave rise to identical α-fluoro-β-hydroxy- aldol products with high diastereoselectivities (95% dr). After removal from the auxiliary α- fluoro-β-hydroxy- products were converted to the corresponding α,β-difluoro products. The synthesis of non symmetric vicinal trifluoro motifs (2S,3R,4S)-314 and (2S,3S,4R)-328 is described in Chapter 3. They were prepared by direct fluorination in three steps of the corresponding (2R,3R,4R)-erythro and (2R,3S,4S)-threo enantio-enriched epoxy-alcohols. The two erythro and threo epoxy-alcohol isomers behave very differently during the first fluorination step and then an attempt to study and rationalise this difference in behaviour is made.
Type
Thesis, PhD Doctor of Philosophy
Collections
  • Chemistry Theses
URI
http://hdl.handle.net/10023/853

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

Advanced Search

Browse

All of RepositoryCommunities & CollectionsBy Issue DateNamesTitlesSubjectsClassificationTypeFunderThis CollectionBy Issue DateNamesTitlesSubjectsClassificationTypeFunder

My Account

Login

Open Access

To find out how you can benefit from open access to research, see our library web pages and Open Access blog. For open access help contact: openaccess@st-andrews.ac.uk.

Accessibility

Read our Accessibility statement.

How to submit research papers

The full text of research papers can be submitted to the repository via Pure, the University's research information system. For help see our guide: How to deposit in Pure.

Electronic thesis deposit

Help with deposit.

Repository help

For repository help contact: Digital-Repository@st-andrews.ac.uk.

Give Feedback

Cookie policy

This site may use cookies. Please see Terms and Conditions.

Usage statistics

COUNTER-compliant statistics on downloads from the repository are available from the IRUS-UK Service. Contact us for information.

© University of St Andrews Library

University of St Andrews is a charity registered in Scotland, No SC013532.

  • Facebook
  • Twitter