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Synlett 1998; 1998(7): 731-732
DOI: 10.1055/s-1998-1768
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A New Approach to 5-Substituted Prolines and 2-Pyrrolecarboxylates

David W. Knight* , Adele L. Redfern, Jeremy Gilmore
  • *Chemistry Department, Cardiff University, P. O. Box 912, Cardiff, CF1 3TB, U.K.; Fax UK (0)1222 874210; E-mail:- knightdw@cf.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Iodocyclisations of the allylic glycinates 7 lead either to the trans- or cis-2,5-disubstituted proline derivatives 8 or 9, depending on the reaction conditions; subsequent treatment of these with DBU in DMF gives the 2-pyrrolecarboxylates 10 and 13 in excellent yields by a double elimination of hydrogen iodide and toluenesulfinic acid.

iodocyclisation - 5-endo-trig - iodopyrrolidine - pyrrole - proline

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