175877-49-3Relevant academic research and scientific papers
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.
