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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.
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|
|Publisher Link: ||http://dx.doi.org/10.1039/C0OB00529K|
|Appears in Collections:||Closed Access (Chemistry)|
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