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Synlett 2015; 26(01): 111-115
DOI: 10.1055/s-0034-1379490
DOI: 10.1055/s-0034-1379490
letter
Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
Further Information
Publication History
Received: 07 September 2014
Accepted after revision: 13 October 2014
Publication Date:
14 November 2014 (online)
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379490. Included are experimental procedures, characterization data, NMR spectra for 6–9, 11, 13, 15, and 17, and atomic coordinates for 23 and 24.
- Supporting Information
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