Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors
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 1477-0520Full text not available from this repository.
Official URL: http://dx.doi.org/10.1039/C1OB06578E
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|
|Official Date:||7 February 2012|
|Page Range:||pp. 1032-1039|
|Access rights to Published version:||Restricted or Subscription Access|
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