Issue 6, 2013
From the journal:

Dalton Transactions

Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis†‡

Gregorio Guisado-Barrios,a   Bianca K. Muñoz,a   Paul C. J. Kamer,*a   Bas Lastdrager,b   Gijs van der Marel,b   Mark Overhand,*b   Marino Vega-Vázquezc  and  Manuel Martin-Pastorc  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
E-mail: pcjk@st-andrews.ac.uk
Fax: +44 (0)1334463808
Tel: +44 (0)1334467258

b Faculty of Science, Leiden Institute of Science, Eisteinweg55, 2333 CC Leiden, Netherlands
E-mail: overhand@chem.leidenuniv.nl
Tel: +31 (0)71 527 4483

c Laboratorio Integral de Dinámica e Estructura de Biomoléculas José R. Carracido, Unidade de Resonancia Magnética, Edificio CACTUS, RIAIDT, Univesidade de Santiago de Compostela, Santiago de Compostela, Spain
E-mail: manuel.martin@usc.es
Tel: +34-981 56 31 00, Ext. 16231

Abstract

The cyclic peptide gramicidin S was used as a rigid template to provide novel peptide-based bisphosphine ligands for transition metal catalysis. Two bisphosphine-coordinated Rh(I) complexes allowed asymmetric hydrogenation with 10–52% ee and the corresponding Pd(II) analogues catalysed asymmetric allylic alkylation with 13–15% ee.

Graphical abstract: Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis

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Article information

DOI
https://doi.org/10.1039/C2DT31782F
Article type
Communication
Submitted
03 Aug 2012
Accepted
27 Nov 2012
First published
28 Nov 2012

Dalton Trans., 2013,42, 1973-1978

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Cyclic decapeptide gramicidin S derivatives containing phosphines: novel ligands for asymmetric catalysis

G. Guisado-Barrios, B. K. Muñoz, P. C. J. Kamer, B. Lastdrager, G. van der Marel, M. Overhand, M. Vega-Vázquez and M. Martin-Pastor, Dalton Trans., 2013, 42, 1973 DOI: 10.1039/C2DT31782F

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