Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine-Ni(II) complexes.
[reaction: see text] We have found the first example of high levels of asymmetric induction (97-74% ee) along with high diastereoselectivity (>99:1-64:36) in dipole-HOMO-/dipolarophile-LUMO-controlled asymmetric 1,3-dipolar cycloaddition reactions between fused azomethine imines and 3-acryloyl-2-oxazolidinone using a chiral BINIM-Ni(II) complex as a chiral Lewis acid catalyst.
Suga
Hiroyuki
H
Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan. sugahio@shinshu-u.ac.jp
Funyu
Akira
A
Kakehi
Akikazu
A
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010081:Oxazolone / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
C517117:3-acryloyl-2-oxazolidinone; D001391:Azo Compounds; D007097:Imines; D008024:Ligands; D009942:Organometallic Compounds; D013882:Thiosemicarbazones; C512188:azomethine; C517119:binaphthyldiimine Ni(II); D010081:Oxazolone; D009532:Nickel