Issue 2, 2010
From the journal:

Organic & Biomolecular Chemistry

Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of γ-glutamyl boletine

Dnyaneshwar Gawasa  and  Uli Kazmaier*a  

* Corresponding authors

a Institut für Organische Chemie, Universität des Saarlandes, D-66123 Saarbrücken, Germany
E-mail: u.kazmaier@mx.uni-saarland.de
Fax: +49 681 302 2409
Tel: +49 681 302 3409

Abstract

A straightforward approach towards γ-glutamyl boletine is described, based on a diastereotopos-differentiating allylic alkylation of chelated amino acid ester enolates. Independent of the configuration of the leaving group in the allylic substrate, the allylation product is obtained as a single stereoisomer. Its configuration is solely controlled by the stereogenic center adjacent to the π-allyl complex formed.

Graphical abstract: Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of γ-glutamyl boletine

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Article information

DOI
https://doi.org/10.1039/B917589J
Article type
Paper
Submitted
26 Aug 2009
Accepted
22 Oct 2009
First published
26 Nov 2009

Org. Biomol. Chem., 2010,8, 457-462

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Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of γ-glutamyl boletine

D. Gawas and U. Kazmaier, Org. Biomol. Chem., 2010, 8, 457 DOI: 10.1039/B917589J

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