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- Title
PyBidine-Cu(OTf)<sub>2</sub>-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu-Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis.
- Authors
Takayoshi Arai; Hiroki Ogawa; Atsuko Awata; Makoto Sato; Megumi Watabe; Masahiro Yamanaka
- Abstract
A bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex catalyzing the endo-selective [3+2] cycloaddition of nitroalkenes with imino esters was applied to the reaction of methyleneindolinones with imino esters to afford spiro[pyrrolidin- 3,3'-oxindole]s in up to 98% ee. X-ray crystallographic analysis of the PyBidine-Cu(OTf)2 complex and DFT calculations suggested that an intermediate Cu enolate of the imino ester reacts with nitroalkenes or methyleneindolinones, which are activated by NH-hydrogen bonding with the PyBidine- Cu(OTf)2 catalyst.
- Subjects
IMIDAZOLIDINES; PYRIDINE derivatives; LEWIS acids; HYDROGEN bonding; IMINO compounds; RING formation (Chemistry); COPPER catalysts; ESTER derivatives
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 5, p1615
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201410782