1187372-06-0Relevant academic research and scientific papers
Efficient pseudo-enantiomeric carbohydrate olefin ligands
Grugel, Holger,Albrecht, Fabian,Minuth, Tobias,Boysen, Mike M. K.
, p. 3780 - 3783 (2012/09/08)
Highly efficient pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites.
Novel olefin-phosphorus hybrid and diene ligands derived from carbohydrates
Grugel, Holger,Minuth, Tobias,Boysen, Mike M. K.
experimental part, p. 3248 - 3258 (2010/11/18)
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. Georg Thieme Verlag Stuttgart New York.
Novel, efficient alkene-phosphinite hybrid ligand based on D-glucose
Minuth, Tobias,Boysen, Mike M. K.
supporting information; experimental part, p. 4212 - 4215 (2009/12/31)
A commercially available 2,3-unsaturated pyranoside, derived from D-glucose, was converted Into a new type of olefin phosphorus chelate ligand in only three steps. Application In rhodium catalyzed conjugate additions of phenylboronic acid to enones led to
