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

Author(s)
Stockton, Kieran
Glover, Stephen
Greatrex, Ben
Publication Date
2015
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.
Citation
Synlett, 26(1), p. 111-115
ISSN
1437-2096
0936-5214
Link
https://hdl.handle.net/1959.11/16535
Language
en
Publisher
Georg Thieme Verlag
Title
Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
Type of document
Journal Article
Entity Type
Publication

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