Loughborough University
Browse

File(s) under permanent embargo

Reason: This item is currently closed access.

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. Steel
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.

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 Chemistry

Volume

9,

Issue

(1)

Pages

297 - 306

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.

Publisher

© The Royal Society of Chemistry

Version

  • NA (Not Applicable or Unknown)

Publication date

2011

Notes

This item is Closed Access

ISSN

1477-0520

Language

  • en

Usage metrics

    Loughborough Publications

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC