Issue 5, 2012

Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors

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.

Graphical abstract: Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors

Supplementary files

Article information

Article type
Paper
Submitted
14 Sep 2011
Accepted
26 Oct 2011
First published
26 Oct 2011

Org. Biomol. Chem., 2012,10, 1032-1039

Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors

K. Griffin, C. Montagne, C. T. Hoang, G. J. Clarkson and M. Shipman, Org. Biomol. Chem., 2012, 10, 1032 DOI: 10.1039/C1OB06578E

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