Imperial College London
Portrait Picture

Dr James A Bull

Faculty of Natural Sciences, Department of Chemistry

Reader in Synthetic Chemistry
 
 
 
//

Contact

 

+44 (0)20 7594 5811j.bull Website

 
 
//

Location

 

501bMolecular Sciences Research HubWhite City Campus

//

Summary

 

Publications

Citation

BibTex format

@article{Davis:2016:10.1021/acs.joc.6b02134,
author = {Davis, OA and Croft, RA and Bull, JA},
doi = {10.1021/acs.joc.6b02134},
journal = {Journal of Organic Chemistry},
pages = {11477--11488},
title = {Synthesis of substituted 1,4-dioxenes through O–H insertion and cyclization using keto-diazo compounds},
url = {http://dx.doi.org/10.1021/acs.joc.6b02134},
volume = {81},
year = {2016}
}
Download

RIS format (EndNote, RefMan)

TY  - JOUR
AB  - 1,4-Dioxenes present interesting potential as synthetic intermediates, and as unusual motifs for incorporation into biologically active compounds. Here, an efficient synthesis of functionalized 1,4-dioxenes is achieved in two steps through a ruthenium catalyzed O–H insertion and base mediated C–O cyclization strategy. From keto-diazo compounds, O–H insertion with bromohydrins, followed by enolization results in cyclization by O–alkylation of the keto-enolate, with excellent selectivity. A variety of substituted bromohydrins and anion-stabilizing functional groups in the diazo-component are tolerated, to afford novel functionalized dioxenes. The use of enantioenriched -bromohydrins provides enantioenriched 1,4-dioxenes.
AU  - Davis,OA
AU  - Croft,RA
AU  - Bull,JA
DO  - 10.1021/acs.joc.6b02134
EP  - 11488
PY  - 2016///
SN  - 1520-6904
SP  - 11477
TI  - Synthesis of substituted 1,4-dioxenes through O–H insertion and cyclization using keto-diazo compounds
T2  - Journal of Organic Chemistry
UR  - http://dx.doi.org/10.1021/acs.joc.6b02134
UR  - http://hdl.handle.net/10044/1/41314
VL  - 81
ER  -
Download