A heterobimetallic Ga/Yb-Schiff base complex for catalytic asymmetric alpha-addition of isocyanides to aldehydes.
Development of a new heterobimetallic Ga(O-iPr)(3)/Yb(OTf)(3)/Schiff base 2d complex for catalytic asymmetric alpha-additions of isocyanides to aldehydes is described. Schiff base 2d derived from o-vanillin was suitable to utilize cationic rare earth metal triflates with good Lewis acidity in bimetallic Schiff base catalysis. The Ga(O-iPr)(3)/Yb(OTf)(3)/Schiff base 2d complex promoted asymmetric alpha-additions of alpha-isocyanoacetamides to aryl, heteroaryl, alkenyl, and alkyl aldehydes in good to excellent enantioselectivity (88-98% ee).
Mihara
Hisashi
H
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Xu
Yingjie
Y
Shepherd
Nicholas E
NE
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000081:Acetamides / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D005708:Gallium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010080:Oxazoles / Q000138:chemical synthesis*; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D015018:Ytterbium / Q000737:chemistry*
D000081:Acetamides; D000447:Aldehydes; D001547:Benzaldehydes; D003486:Cyanides; D009942:Organometallic Compounds; D010080:Oxazoles; D012545:Schiff Bases; D005708:Gallium; C100058:vanillin; D015018:Ytterbium