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Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors
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Griffin, Karen, Montagne, Cyril, Hoang, Cam Thuy, Clarkson, Guy J. and Shipman, Michael (2012) Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors. Organic & Biomolecular Chemistry, Vol.10 (No.5). pp. 1032-1039. doi:10.1039/c1ob06578e ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/C1OB06578E
Abstract
2-Methyleneaziridines can be tethered to a variety of alkene or alkyne acceptors through the saturated carbon of the heterocyclic ring by application of a simple lithiation/alkylation sequence (8 examples, 31–59%). Treatment of the resultant alkene bearing substrates with BF3·OEt2 leads to cis-octahydrocyclopenta[c]pyrroles in which up to four contiguous stereocentres are created in a diastereocontrolled manner after reductive work-up. Using an alkyne based substrate, a 2,4,5,6-tetrahydrocyclopenta[c]pyrrole is produced by rapid tautomerisation of the initially formed bisenamine. Evidence that these (3 + 2) ‘cycloadditions’ proceed in a stepwise manner via a 2-aminoallyl cation is presented.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||
Publisher: | Royal Society of Chemistry | ||||
ISSN: | 1477-0520 | ||||
Official Date: | 7 February 2012 | ||||
Dates: |
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Volume: | Vol.10 | ||||
Number: | No.5 | ||||
Page Range: | pp. 1032-1039 | ||||
DOI: | 10.1039/c1ob06578e | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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