title: PyBidine/copper catalyst: asymmetric exo'-selective [3+2] cycloaddition using imino ester and electrophilic indole.
abstract: Electrophilic indoles having two electron-withdrawing groups undergo nucleophilic attack at C2 and electrophilic functionalization at C3. This is the first enantioselective formal [3+2] cycloaddition using electrophilic indoles. The PyBidine/Cu catalyst smoothly promoted highly enantio- and exo'-selective [3+2] cycloaddition using imino esters and 3-nitroindoles. This reaction provides a method for the preparation of diverse and complex chiral pyrroloindoline compounds.
authors: Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522 (Japan) http://synthesis.chem.chiba-u.jp/index.htm.
authors: Atsuko
authors: A
authors: Awata
authors: Takayoshi
authors: T
authors: Arai
mesh_terms: D000627:Aminophenols / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004952:Esters; D048289:Imidazolidines / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000627:Aminophenols; D004952:Esters; D048289:Imidazolidines; D007211:Indoles; D011725:Pyridines; D003300:Copper; C023666:pyridine
keywords: asymmetric catalysis; copper; cycloaddition; heterocycles; synthetic methods