Use this URL to cite or link to this record in EThOS:
Title: Investigation of diastereomeric induction in the Diels-Alder reactions of acylnitroso dienophiles
Author: Lochrie, Ian Stewart Tolmie
ISNI:       0000 0001 3611 9036
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 1996
Availability of Full Text:
Access from EThOS:
Access from Institution:
Oxidation of hydroxamic acids, and also related N-hydroxyureas and N-hydroxycarbamates, gives acylnitroso dienophiles. These are highly reactive species and cannot be isolated, however they can be trapped with dienes, undergoing hetero Diels-Alder reactions to give cycloadducts. The aim of this project was to investigate diastereomeric induction in the hetero-Diels-Alder reactions of acylnitroso dienophiles by attaching them to chiral auxiliaries. The chiral auxiliaries used were mainly based on 1,2-trans-cyclohexylamines or 1,2-trans-cyclohexanols and used a large equatorial 2-substituent to shield one face of the dienophile. It was hoped that intramolecular hydrogen bonding in nitrosoformamide dienophile 234 would restrict the rotation of the dienophile and hence increase the diastereoselectivity of the cycloaddition, in comparison with nitrosoformate dienophiles 238 and 292 which cannot have this intramolecular hydrogen bonding.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry