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Cycloaddition of homochiral dihydroimidazoles: a 1,3-dipolar cycloaddition route to optically active pyrrolo [1,2-a] imidazoles
journal contribution
posted on 2014-08-27, 12:50 authored by Ray Jones, Kevin J. Howard, John S. Snaith, Alexander J. Blake, Wang-Shei Li, Peter J. SteelN-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.
Funding
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.)
History
School
- Science
Department
- Chemistry
Published in
Organic and Biomolecular ChemistryVolume
9,Issue
(1)Pages
297 - 306Citation
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.Publisher
© The Royal Society of ChemistryVersion
- NA (Not Applicable or Unknown)
Publication date
2011Notes
This item is Closed AccessISSN
1477-0520Publisher version
Language
- en