test Browse by Author Names Browse by Titles of Works Browse by Subjects of Works Browse by Issue Dates of Works
       

Advanced Search
Home   
 
Browse   
Communities
& Collections
  
Issue Date   
Author   
Title   
Subject   
 
Sign on to:   
Receive email
updates
  
My Account
authorized users
  
Edit Profile   
 
Help   
About T-Space   

T-Space at The University of Toronto Libraries >
School of Graduate Studies - Theses >
Master >

Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/24246

Title: Studies towards Developing Diastereoselective SN1 Reactions of α-Keto Carbocations
Authors: Dubland, Joshua
Advisor: Taylor, Mark S.
Department: Chemistry
Keywords: diastereoselective SN1 reaction
alpha-keto carbocation
nucleophilic substitution reaction
carbon-carbon bond forming reaction
carbon-heteroatom bond forming reaction
chiral auxiliary
asymmetric synthesis
Lewis acid-mediated
Bronsted acid-mediated
silver-mediated
organic chemistry
leaving group
ester
amide
imide
Issue Date: 6-Apr-2010
Abstract: Although α-keto carbocations have been demonstrated to be viable intermediates in solvolysis reactions, their applications in synthesis are scarce. These species can be considered to be equivalent to “reversed polarity” enolates and, as such, could be useful for the asymmetric formation of carbon-carbon and carbon-heteroatom bonds. In principle, facial selectivity in additions to α-keto carbocations may be induced using easily removed ester, amide, or imide chiral auxiliaries. Efforts to achieve such diastereoselective SN1 reactions of α-keto carbocations are described herein.
URI: http://hdl.handle.net/1807/24246
Appears in Collections:Master
Department of Chemistry - Master theses

Files in This Item:

File Description SizeFormat
Dubland_Joshua_A_201003_MSc_thesis.pdf3.61 MBAdobe PDF
View/Open

Items in T-Space are protected by copyright, with all rights reserved, unless otherwise indicated.

uoft