title: Side-arm-promoted highly enantioselective ring-opening reactions and kinetic resolution of donor-acceptor cyclopropanes with amines.
abstract: A Ni-catalyzed asymmetric ring-opening reaction of 2-substituted cyclopropane-1,1-dicarboxylates with aliphatic amines has been accomplished using the chiral indane-trisoxazoline (In-TOX) ligand. This highly enantioselective reaction provides an efficient approach to a variety of chiral γ-substituted γ-amino acid derivatives, which are readily transformed into multifunctionalized piperidines and γ-lactams. The single-crystal X-ray structure of the TOX-Ni complex is provided, and the role of the side arm in the chiral ligand is discussed.
authors.affiliation: The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, PR China.
authors.forename: You-Yun
authors.initials: YY
authors.lastname: Zhou
authors.forename: Li-Jia
authors.initials: LJ
authors.lastname: Wang
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Xiu-Li
authors.initials: XL
authors.lastname: Sun
authors.forename: Yong
authors.initials: Y
authors.lastname: Tang
mesh_terms: D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000596:Amino Acids; D003521:Cyclopropanes; D009942:Organometallic Compounds; D009532:Nickel