Efficient pseudo-enantiomeric carbohydrate olefin ligands.
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.
Institute of Organic Chemistry, Gottfried-Wilhelm-Leibniz University of Hannover , D-30167 Hannover, Germany.
Holger
H
Grugel
Fabian
F
Albrecht
Tobias
T
Minuth
Mike M K
MM
Boysen
D000475:Alkenes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D002241:Carbohydrates; D008024:Ligands; D005947:Glucose; D005690:Galactose