Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes.

Nandkishor Chandan, Amber L Thompson, Mark G Moloney

The Department of Chemistry, Chemistry Research Laboratory, The University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.

Organic & biomolecular chemistry 2012 Oct 21

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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.

Citation

Nandkishor Chandan, Amber L Thompson, Mark G Moloney. Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes. Organic & biomolecular chemistry. 2012 Oct 21;10(39):7863-8