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Issue 43, 2012
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Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

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Abstract

Sodium TMP-zincate, [(TMEDA)Na(TMP)(tBu)Zn(tBu)], can deproto-zincate N-Boc pyrrolidine at ambient temperature in hexane solution, whereas in toluene the captured α-carbanion of the heterocycle attacks the solvent setting off a cascade of reactions that ultimately produce a pyrrolidine-substituted enolate.

Graphical abstract: Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

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Publication details

The article was received on 10 Mar 2012, accepted on 04 Apr 2012 and first published on 05 Apr 2012


Article type: Communication
DOI: 10.1039/C2CC31793A
Citation: Chem. Commun., 2012,48, 5265-5267
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    Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency

    J. A. Garden, A. R. Kennedy, R. E. Mulvey and S. D. Robertson, Chem. Commun., 2012, 48, 5265
    DOI: 10.1039/C2CC31793A

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