Unprecedented selectivity via electronic substrate recognition in the 1,4-addition to cyclic olefins using a chiral disulfoxide rhodium catalyst.
From zero to hero? Sulfoxides are generally not considered useful ligand entities in asymmetric metal catalysis. However, a chiral disulfoxide as a chelating ligand in the rhodium-catalyzed 1,4-addition of aryl boronic acids to cyclic, alpha,beta-unsaturated ketones and esters gives impressive catalytic results, thus opening the door to future applications of this new chiral ligand class.
Bürgi
Justus J
JJ
Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
Mariz
Ronaldo
R
Gatti
Michele
M
Drinkel
Emma
E
Luan
Xinjun
X
Blumentritt
Sascha
S
Linden
Anthony
A
Dorta
Reto
R
D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
D001897:Boronic Acids; D003516:Cycloparaffins; D004952:Esters; D007659:Ketones; D010720:Phosphines; D013454:Sulfoxides; D012238:Rhodium; C044646:phosphine