Issue 12, 2003
From the journal:

Chemical Communications

Aziridinyl anions from a chiral, nonracemic 2-isopropylidineaziridine: surprisingly diastereoselective alkylation reactions

J. F. Hayes,a   N. Prévost,b   I. Prokeš,b   M. Shipman,*b   A. M. Z. Slawinc  and  H. Twinb  

* Corresponding authors

a GlaxoSmithKline, Old Powder Mills, Tonbridge, Kent, UK

b School of Chemistry, University of Exeter, Stocker Road, Exeter, Devon, UK
E-mail: m.shipman@exeter.ac.uk
Fax: +44 1392 263434
Tel: +44 1392 263469

c School of Chemistry, University of St. Andrews, Purdie Building, St. Andrews, Fife, UK

Abstract

Lithiation and alkylation of a 2-isopropylidineaziridine bearing an (S)-α-methylbenzyl group on nitrogen proceeds with high levels of diastereocontrol (80–90% de).

Graphical abstract: Aziridinyl anions from a chiral, nonracemic 2-isopropylidineaziridine: surprisingly diastereoselective alkylation reactions

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Article information

DOI
https://doi.org/10.1039/B303252C
Article type
Communication
Submitted
26 Mar 2003
Accepted
28 Apr 2003
First published
20 May 2003

Chem. Commun., 2003, 1344-1345

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Aziridinyl anions from a chiral, nonracemic 2-isopropylidineaziridine: surprisingly diastereoselective alkylation reactions

J. F. Hayes, N. Prévost, I. Prokeš, M. Shipman, A. M. Z. Slawin and H. Twin, Chem. Commun., 2003, 1344 DOI: 10.1039/B303252C

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