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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. 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 |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Journal or Publication Title: | Organic & Biomolecular Chemistry |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 1477-0520 |
| Date: | 7 February 2012 |
| Volume: | Vol.10 |
| Number: | No.5 |
| Page Range: | pp. 1032-1039 |
| Identification Number: | 10.1039/c1ob06578e |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| URI: | http://wrap.warwick.ac.uk/id/eprint/48024 |
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