title: Proline catalyzed sequential α-aminooxylation or -amination/reductive cyclization of o-nitrohydrocinnamaldehydes: a high yield synthesis of chiral 3-substituted tetrahydroquinolines.
abstract: A new sequential organocatalytic method for the synthesis of chiral 3-substituted (X = OH, NH2) tetrahydroquinoline derivatives (THQs) [ee up to 99%, yield up to 87%] based on α-aminooxylation or -amination followed by reductive cyclization of o-nitrohydrocinnamaldehydes has been described. This methodology has been efficiently demonstrated in the synthesis of two important bioactive molecules namely (-)-sumanirole (96% ee) and 1-[(S)-3-(dimethylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone (92% ee).
authors: Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411008, India.
authors: Varun
authors: V
authors: Rawat
authors: B Senthil
authors: BS
authors: Kumar
authors: Arumugam
authors: A
authors: Sudalai
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D010084:Oxidation-Reduction; D011392:Proline / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D011804:Quinolines; D011392:Proline; C542964:1,2,3,4-tetrahydroquinoline