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An enantioselective route to pyrrolidines: removal of the chiral template from homochiral pyrroloimidazoles |
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| Authors: | Raymond C.F. Jones Kevin J. HowardJohn S. Snaith Alexander J. BlakeWang-Shei Li Peter J. Steel |
| Affiliation: | a Department of Chemistry, Loughborough University, Loughborough, Leics. LE11 3TU, UK b Department of Chemistry, The Open University, Walton Hall, Milton Keynes MK7 6AA, UK c Department of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK d Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand |
| Abstract: | Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines. |
| Keywords: | Pyrrolidine Pyrroloimidazole Enantioselective Pyrrolizidine Indolizidine |
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