Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/16535
Title: Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
Contributor(s): Stockton, Kieran (author); Glover, Stephen (author); Greatrex, Ben (author)orcid 
Publication Date: 2015
Open Access: Yes
DOI: 10.1055/s-0034-1379490
Handle Link: https://hdl.handle.net/1959.11/16535
Open Access Link: https://doi.org/10.1055/s-0034-1379490
Abstract: Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.
Publication Type: Journal Article
Source of Publication: Synlett, 26(1), p. 111-115
Publisher: Georg Thieme Verlag
Place of Publication: Germany
ISSN: 1437-2096
0936-5214
Field of Research (FOR): 030503 Organic Chemical Synthesis
030502 Natural Products Chemistry
030505 Physical Organic Chemistry
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Statistics to Oct 2018: Visitors: 353
Views: 446
Downloads: 0
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

Files in This Item:
2 files
File Description SizeFormat 
Show full item record

SCOPUSTM   
Citations

1
checked on Nov 30, 2018

Page view(s)

94
checked on Mar 3, 2019
Google Media

Google ScholarTM

Check

Altmetric

SCOPUSTM   
Citations

 

WEB OF SCIENCETM
Citations

 

Items in Research UNE are protected by copyright, with all rights reserved, unless otherwise indicated.