New catalysts for the asymmetric hydrosilylation of ketones discovered by mass spectrometry screening.
A method for determining enantiomeric excess by mass spectrometry was employed to screen a family of chiral phosphite P,N-ligands for activity in the rhodium-catalyzed asymmetric hydrosilylation of ketones. The identification of an effective set of ligands was followed by preliminary studies of the reaction scope and mechanism. Asymmetric induction of 84-88% ee for larger-scale reactions was observed, which is close to the level of the best alternative catalysts previously discovered. The screening method was shown to be applicable to a variety of substrates without the need for special optimization.
Yao
Sulan
S
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Meng
Jun-Cai
JC
Siuzdak
Gary
G
Finn
M G
MG
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D008024:Ligands; D012821:Silanes; D012238:Rhodium