Synthesis and Reactions of 2-[1-Methyl-1-(pyrrolidin-2-yl)ethyl]-1H-pyrrole and Some Derivatives with Aldehydes: Chiral Structures Combining a Secondary-Amine Group with an 1H-Pyrrole Moiety as Excellent H-Bond Donor

Authors

  • Anca Pordea,

    1. Institut de chimie, Université de Neuchâtel, Avenue Bellevaux 51, CH-2000 Neuchâtel, (phone: +41 (0)32 718 2428; fax +41 (0)32 718 2511)
    2. New address since 1 August, 2012: Department of Chemical & Environmental Engineering, University of Nottingham, University Park, Nottingham NG7 2RD, UK (phone: +44 (0)115 951 4640)
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  • Helen Stoeckli-Evans,

    1. Institut de physique, Université de Neuchâtel, Avenue Bellevaux 51, CH-2000 Neuchâtel, (phone: +41 (0)32 718 2426)
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  • Claudio Dalvit,

    1. Service analytique facultaire, Université de Neuchâtel, Avenue Bellevaux 51, CH-2000 Neuchâtel, (phone: +41 (0)32 718 2435)
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  • Reinhard Neier

    Corresponding author
    1. Institut de chimie, Université de Neuchâtel, Avenue Bellevaux 51, CH-2000 Neuchâtel, (phone: +41 (0)32 718 2428; fax +41 (0)32 718 2511)
    • Institut de chimie, Université de Neuchâtel, Avenue Bellevaux 51, CH-2000 Neuchâtel, (phone: +41 (0)32 718 2428; fax +41 (0)32 718 2511)

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Abstract

The synthesis of compound 2 and its derivatives 6 and 8 combining a pyrrolidine ring with an 1H-pyrrole unit is described (Scheme 2). Their attempted usability as organocatalysts was not successful. Reacting these simple pyrrolidine derivatives with cinnamaldehyde led to the tricyclic products 3b, 9b, and 10b first (Scheme 1, Fig. 2). The final, major products were the pyrrolo-indolizidine tricycles 3a, 9a, and 10a obtained via the iminium ion reacting intramolecularly with the nucleophilic β-position of the 1H-pyrrole moiety (cf. Scheme 1).

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