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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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Article information


Submitted
20 Jul 2012
Accepted
15 Aug 2012
First published
15 Aug 2012

Org. Biomol. Chem., 2012,10, 7863-7868
Article type
Communication

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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