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Issue 39, 2012
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Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes

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Abstract

Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.

Graphical abstract: Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes

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Publication details

The article was received on 20 Jul 2012, accepted on 15 Aug 2012 and first published on 15 Aug 2012


Article type: Communication
DOI: 10.1039/C2OB26423D
Citation: Org. Biomol. Chem., 2012,10, 7863-7868
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    Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes

    N. Chandan, A. L. Thompson and M. G. Moloney, Org. Biomol. Chem., 2012, 10, 7863
    DOI: 10.1039/C2OB26423D

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