Issue 43, 2012
From the journal:

Chemical Communications

Ambient temperature zincation of N-Boc pyrrolidine and its solvent dependency†

Jennifer A. Garden,a   Alan R. Kennedy,a   Robert E. Mulvey*a  and  Stuart D. Robertsona  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: r.e.mulvey@strath.ac.uk

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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Article information

DOI
https://doi.org/10.1039/C2CC31793A
Article type
Communication
Submitted
10 Mar 2012
Accepted
04 Apr 2012
First published
05 Apr 2012

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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