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Title: Cycloaddition of homochiral dihydroimidazoles: a 1,3-dipolar cycloaddition route to optically active pyrrolo [1,2-a] imidazoles
Authors: Jones, Raymond C.F.
Howard, Kevin J.
Snaith, John S.
Blake, Alexander J.
Li, Wang-Shei
Steel, Peter J.
Issue Date: 2011
Publisher: © The Royal Society of Chemistry
Citation: JONES, R.C.F. ... et al., 2011. Cycloaddition of homochiral dihydroimidazoles: a 1,3-dipolar cycloaddition route to optically active pyrrolo [1,2-a] imidazoles. Organic and Biomolecular Chemistry, 9(1), pp.297-306.
Abstract: N-Alkylation of optically active 1-benzyl-4-phenyl-4,5-dihydroimidazole with active alkyl halides and treatment of the so-formed 4,5-dihydroimidazolium ions with DBU in the presence of a range of electron-deficient alkene dipolarophiles, constitutes a ‘one-pot’ cascade terminating in a 1,3-dipolar cycloaddition reaction that affords optically active pyrrolo[1,2-a]imidazoles. Three bonds of the so-formed pyrrolidine moiety are constructed in this cascade. The cycloaddition follows an endo approach of dipole and dipolarophile with anti geometry of the dipole and facial selectivity derived from the phenyl substituent. Inter- and intramolecular cycloaddition modes are observed.
Description: This item is Closed Access
Sponsor: We thank EPSRC for postdoctoral funding (J.S.S., K.J.H.), University of Nottingham for a studentship (K.J.H.), Rhone- Poulenc Agriculture for additional financial support (K.J.H.)
Version: Closed access
DOI: 10.1039/C0OB00529K
URI: https://dspace.lboro.ac.uk/2134/15686
Publisher Link: http://dx.doi.org/10.1039/C0OB00529K
ISSN: 1477-0520
Appears in Collections:Closed Access (Chemistry)

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