Synthesis and Diels-Alder reaction of novel C2-symmetric chiral dienes
Synthesis and Diels-Alder reaction of novel C2-symmetric chiral dienes
The development and synthesis of a novel class of C2-symmetric outer ring dienes is described. Six novel chiral dienes, based upon the butane diacetal group, were synt4hsised from tartaric acid derivatives and the Diels-Alder reaction of three of these dienes was carried out. The diastereoselectivity of the Diels-Alder reaction with a range of dienophiles was investigated. The removal of the chiral auxiliary after the Diels-Alder reaction was also investigated.
In an additional study tris-1,1,1-(hydroxymethyl)ethane was converted to a series of mono- and disubstituted derivatives. An indirect protocol, utilising chemoselective reactions, for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated tris-1,1,1-(hydroxymethyl)ethane containing a protected aldehyde unit.
University of Southampton
Clarke, Philip John
678492c4-acd2-48f5-adfc-f71c6285cd42
2005
Clarke, Philip John
678492c4-acd2-48f5-adfc-f71c6285cd42
Clarke, Philip John
(2005)
Synthesis and Diels-Alder reaction of novel C2-symmetric chiral dienes.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
Abstract
The development and synthesis of a novel class of C2-symmetric outer ring dienes is described. Six novel chiral dienes, based upon the butane diacetal group, were synt4hsised from tartaric acid derivatives and the Diels-Alder reaction of three of these dienes was carried out. The diastereoselectivity of the Diels-Alder reaction with a range of dienophiles was investigated. The removal of the chiral auxiliary after the Diels-Alder reaction was also investigated.
In an additional study tris-1,1,1-(hydroxymethyl)ethane was converted to a series of mono- and disubstituted derivatives. An indirect protocol, utilising chemoselective reactions, for the differentiation of the alcohol groups was employed for the synthesis of partially and fully differentiated tris-1,1,1-(hydroxymethyl)ethane containing a protected aldehyde unit.
Text
983016.pdf
- Version of Record
More information
Published date: 2005
Identifiers
Local EPrints ID: 465694
URI: http://eprints.soton.ac.uk/id/eprint/465694
PURE UUID: 14cf7769-9f9f-45a4-a97f-2544b735bb39
Catalogue record
Date deposited: 05 Jul 2022 02:36
Last modified: 16 Mar 2024 20:19
Export record
Contributors
Author:
Philip John Clarke
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics