title: Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.
abstract: An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate to good yields (34-78%) and excellent stereoselectivities (87-99% ee, up to >20 : 1 d.r.).
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany. enders@rwth-aachen.de.
authors.forename: Qijian
authors.initials: Q
authors.lastname: Ni
authors.forename: Xiaoxiao
authors.initials: X
authors.lastname: Song
authors.forename: Jiawen
authors.initials: J
authors.lastname: Xiong
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders
mesh_terms: D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D011744:Pyrimidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D007097:Imines; D007769:Lactams; D011744:Pyrimidinones; D013844:Thiazoles; C030011:carbene; D008697:Methane