Regioselective and enantiospecific rhodium-catalyzed allylic amination with N-(arylsulfonyl)anilines.
[reaction: see text]. The regioselective and enantiospecific rhodium-catalyzed allylic amination of secondary allylic carbonates 1 with N-(arylsulfonyl)anilines provides a convenient process for the construction of arylamines 2. This method, in conjunction with ring-closing metathesis and radical cyclization reactions, allows the direct construction of biologically relevant pharmacophores as exemplified by the construction of dihydroquinoline and dihydrobenzo[b]indoline derivatives.
Evans
P A
PA
Department of Chemistry, Indiana University, Bloomington, Indiana 47405, USA. paevans@indiana.edu
Robinson
J E
JE
Moffett
K K
KK
D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis; D011804:Quinolines / Q000138:chemical synthesis; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D000814:Aniline Compounds; D007211:Indoles; D011804:Quinolines; D013449:Sulfonamides; D012238:Rhodium