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Synlett 1999; 1999(12): 1871-1874
DOI: 10.1055/s-1999-2966
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An Expedient Synthesis of Pyrrole Derivatives by Reaction of Lithiated Methoxyallenes with Imines

Marlyse Okala Amombo* , Arndt Hausherr, Hans-Ulrich Reissig
  • *Institut für Organische Chemie der Technischen Universität Dresden, D-01062, Germany; Fax + 49(0)3 51/4 63-70 30; E-mail: Hans.Reissig@chemie.tu-dresden.de
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Publication Date:
31 December 1999 (online)

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Addition of lithiated methoxyallene 2 to imines provided the expected allenyl amines in good yield. These could be cyclized with base or with silver nitrate to a variety of 2,5-dihydropyrrole derivatives. Selected examples describe their conversion to pyrrolidin-3-ones or 3-methoxypyrroles. Most importantly, this [3 + 2]cyclization method could also be applied to the synthesis of 2,5-disubstituted derivatives such as 26-28 and also to the preparation of the enantiopure compound 23.

methoxyallene - imine - allenyl amine - 2,5-dihydropyrrole - pyrrolidin-3-one - 3-methoxypyrrole