title: An enantioselective organocatalyzed aza-Morita-Baylis-Hillman reaction of isatin-derived ketimines with acrolein.
abstract: A highly enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction of isatin-derived ketimines with acrolein was established using β-isocupreidine (β-ICD) or α-isocupreine (α-ICPN) as a chiral acid-base organocatalyst. The present protocol readily furnished (S) or (R)-aza-MBH adducts with a chiral tetrasubstituted carbon stereogenic center in up to 98% ee.
authors.affiliation: The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan. taki@sanken.osaka-u.ac.jp.
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Yoshida
authors.forename: Makoto
authors.initials: M
authors.lastname: Sako
authors.forename: Kenta
authors.initials: K
authors.lastname: Kishi
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Sasai
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
authors.forename: Shinobu
authors.initials: S
authors.lastname: Takizawa
mesh_terms: D000171:Acrolein / Q000737:chemistry*; D002384:Catalysis; D006912:Hydroxyquinolines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006912:Hydroxyquinolines; D007097:Imines; D009570:Nitriles; D011812:Quinuclidines; C517075:beta-isocupreidine; C542835:ketimine; D000171:Acrolein; D007510:Isatin