Iridium/monodentate phosphoramidite catalyzed asymmetric hydrogenation of N-aryl imines.
Asymmetric hydrogenation of N-aryl acetophenone imines using iridium/PipPhos leads to very high enantioselectivities up to >99% depending on the presence of electron-donating substituents in the 2-, 3-, and 5-position of the aryl ring. If the substituent is 2-methoxy, the resultant secondary amines are easily oxidatively deprotected using trichloroisocyanuric acid to give the primary amines in good yield with full retention of enantioselectivity.
Mrsić
Natasa
N
University of Groningen, Stratingh Institute for Chemistry, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
de Vries
Johannes G
JG
D000098:Acetophenones / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D006865:Hydrogenation; D007097:Imines / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000098:Acetophenones; D000814:Aniline Compounds; D007097:Imines; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D007495:Iridium