Stereoselective synthesis of indoline, tetrahydroquinoline, and tetrahydrobenzazepine derivatives from o-bromophenyl N-tert-butylsulfinyl aldimines.
The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (−)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).
Juan Alberto
JA
Sirvent
Francisco
F
Foubelo
Miguel
M
Yus
D000473:Alkanes / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000473:Alkanes; D001552:Benzazepines; D007097:Imines; D007211:Indoles; D007769:Lactams; D011804:Quinolines; D013438:Sulfhydryl Compounds; C057812:indoline; D003300:Copper; C542964:1,2,3,4-tetrahydroquinoline