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Synthesis 2010(19): 3248-3258  
DOI: 10.1055/s-0030-1258190
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Olefin-Phosphorus Hybrid and Diene Ligands Derived from Carbohydrates

Holger Grugel, Tobias Minuth, Mike M. K. Boysen*
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Fax: +49(511)7623011; e-Mail: mike.boysen@oci.uni-hannover.de;
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Publication History

Received 30 April 2010
Publication Date:
05 August 2010 (online)

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Abstract

Starting from readily available monosaccharides d-glucose and d-arabinose, a family of novel chiral diene and olefin-phosphinite hybrid ligands has been designed. These ligands were prepared by attaching phosphinite or allylic donor sites onto unsaturated carbohydrate scaffolds. In rhodium(I)-catalysed conjugate addition of boronic acids to enones, the olefin-phosphinite hybrids gave products in up to 99% ee and above, whereas the dienes only led to modest enantioselectivity. However, by shifting the allylic donor sites from position 4 of the pyranose to the anomeric centre, an unexpected reversal of the stereoinduction process was observed.

Key words

carbohydrates - ligand design - asymmetric catalysis - rhodium - boron

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