Synthesis of substituted 1,4-dioxenes through O–H insertion and cyclization using keto-diazo compounds
File(s)
Accepted version
Supporting information
Author(s)
Davis, OA
Croft, RA
Bull, JA
Type
Journal Article
Abstract
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.
Date Issued
2016-10-10
Date Acceptance
2016-10-10
Citation
Journal of Organic Chemistry, 2016, 81 (22), pp.11477-11488
ISSN
1520-6904
Publisher
American Chemical Society
Start Page
11477
End Page
11488
Journal / Book Title
Journal of Organic Chemistry
Volume
81
Issue
22
Copyright Statement
© 2016 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.6b02134
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
Grant Number
EP/J001538/1
EP/K503733/1
UF140161
Subjects
Organic Chemistry
0304 Medicinal And Biomolecular Chemistry
0305 Organic Chemistry
0302 Inorganic Chemistry
Publication Status
Published