Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates

Title
Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
Publication Date
2015
Author(s)
Stockton, Kieran
Glover, Stephen
( author )
OrcID: https://orcid.org/0000-0002-9344-8669
Email: sglover@une.edu.au
UNE Id une-id:sglover
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
Georg Thieme Verlag
Place of publication
Germany
DOI
10.1055/s-0034-1379490
UNE publication id
une:16772
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.
Link
Citation
Synlett, 26(1), p. 111-115
ISSN
1437-2096
0936-5214
Start page
111
End page
115

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