Asymmetric synthesis of tetrahydroquinolin-3-ols via CoCl2-catalyzed reductive cyclization of nitro cyclic sulfites with NaBH4.
A new method for the construction of chiral 3-substituted tetrahydroquinoline derivatives based on asymmetric dihydroxylation and CoCl(2)-catalyzed reductive cyclization of nitro cyclic sulfites with NaBH(4) has been described with high optical purities. This method has been successfully applied in the formal synthesis of PNU 95666E and anachelin H chromophore.
Jagdale
Arun R
AR
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune-411 008, India.
Reddy
R Santhosh
RS
Sudalai
Arumugam
A
D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001894:Borohydrides / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011806:Quinolinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013447:Sulfites / Q000737:chemistry*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry
D001562:Benzimidazoles; D001894:Borohydrides; D009574:Nitro Compounds; D009842:Oligopeptides; D011806:Quinolinium Compounds; D013447:Sulfites; D044005:Tetrahydroisoquinolines; C525348:anachelin H; C108539:U 95666E; D003035:Cobalt; C025364:sodium borohydride