Highly enantioselective Ir-catalyzed hydrogenation of exocyclic enamines

[Ir(COD)Cl]2/MeO-BiPhep/I2 catalyst system is highly effective for the asymmetric hydrogenation of exocyclic enamines with high enantioselectivities (up to 96% ee).

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(R)-2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1-phenylethanoneC17H17NO[α]D = −96.6 (c 0.54, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-1-(1,2,3,4-Tetrahydroquinolin-2-yl)propan-2-oneC12H15NO[α]D = −87.3 (c 1.06, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-1-(1,2,3,4-Tetrahydroquinolin-2-yl)pentan-2-oneC14H19NO[α]D = −93.1 (c 1.01, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-1-(4-(Trifluoromethyl)phenyl)-2-(1,2,3,4-tetrahydroquinolin-2-yl)ethanoneC18H16F3NO[α]D = −80.0 (c 1.12, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1-(4-isopropylphenyl)ethanoneC20H23NO[α]D = −70.3 (c 1.32, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1-o-tolylethanoneC18H19NO[α]D = −94.9 (c 1.06, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1-(naphthalen-1-yl)ethanoneC21H19NO[α]D = −145.7 (c1.12, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-1-(1,2,3,4-Tetrahydroquinolin-2-yl)-4-phenylbutan-2-oneC19H21NO[α]D = −57.8 (c 1.12, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(6-Fluoro-1,2,3,4-tetrahydroquinolin-2-yl)-1-phenylethanoneC17H16FNO[α]D = −48.9 (c 0.50, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(1,2,3,4-Tetrahydro-6-methylquinolin-2-yl)-1-phenylethanoneC18H19NO[α]D = −48.7 (c 0.34, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-Methyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetateC12H15NO2[α]D = −77.2 (c 0.74, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-N,N-Diethyl-2-(1,2,3,4-tetrahydroquinolin-2-yl)acetamideC15H22N2O[α]D = −69.8 (c 1.00, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-(1,2,3,4-Tetrahydroquinolin-2-yl)-1-(3,4-dimethoxyphenyl)ethanoneC19H21NO3[α]D = −53.9 (c 1.21, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(S)-2-(3,4-Dimethoxyphenethyl)-1,2,3,4-tetrahydroquinolineC19H23NO2[α]D = −59.9 (c 1.00, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-(3,4-Dimethoxyphenethyl)-1,2,3,4-tetrahydroquinolineC20H25NO2[α]D = −27.2 (c 0.87, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)