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Iridium/monodentate phosphoramidite catalyzed asymmetric hydrogenation of N-aryl imines
Natasa Mrsić1, Adriaan J Minnaard, Ben L Feringa
1University of Groningen, Stratingh Institute for Chemistry, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Abstract:
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.
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