Utilization of IndPHOX-ligands in palladium-catalysed asymmetric allylic aminations

IndPHOX (indole phosphine oxazoline) ligands were utilized in palladium-catalysed asymmetric allylic amination with different N-nucleophiles. The reactions proceeded well and excellent enantioselectivities of up to 99% were achieved.

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(S)-N-(2-Hydroxy-2,4-dimethylpentan-3-yl)-1H-indole-3-carboxamideC16H22N2O2[α]D20=-12.3 (c 0.3, MeOH)Source of chirality: l-valinolAbsolute configuration: (S)

(S)-N-(1-Hydroxy-3,3-dimethylbutan-2-yl)-1H-indole-3-carboxamideC15H20N2O2[α]D20=-4.0 (c 0.6, MeOH)Source of chirality: l-tert-leucinolAbsolute configuration: (S)

(S)-2-(1H-Indol-3-yl)-4-isopropyl-5,5-dimethyl-4,5-dihydrooxazoleC16H20N2O[α]D20=-51.7 (c 0.3, CHCl3)Source of chirality: l-valinolAbsolute configuration: (S)

(S)-4-tert-Butyl-2-(1H-indol-3-yl)-4,5-dihydrooxazoleC15H18N2O[α]D20=-61.7 (c 0.3, CHCl3)Source of chirality: l-tert-leucinolAbsolute configuration: (S)

(S)-4-Isopropyl-2-(1-(methoxymethyl)-1H-indol-3-yl)-5,5-dimethyl-4,5-dihydrooxazoleC18H24N2O2[α]D20=-51.0 (c 0.3, CHCl3)Source of chirality: l-valinolAbsolute configuration: (S)

(S)-4-tert-Butyl-2-(1-(methoxymethyl)-1H-indol-3-yl)-4,5-dihydrooxazoleC17H22N2O2[α]D20=-60.5 (c 0.6, CHCl3)Source of chirality: l-tert-leucinolAbsolute configuration: (S)

(S)-2-(2-(Diphenylphosphino)-1-(methoxymethyl)-1H-indol-3-yl)-4-isopropyl-5,5-dimethyl-4,5-dihydrooxazoleC30H33N2O2P[α]D20=-48.6 (c 0.63, CHCl3)Source of chirality: l-valinolAbsolute configuration: (S)

(S)-4-tert-Butyl-2-(2-(diphenylphosphino)-1-(methoxymethyl)-1H-indol-3-yl)-4,5-dihydrooxazoleC28H31N2O2P[α]D20=-156.3 (c 0.6, CHCl3)Source of chirality: l-tert-leucinolAbsolute configuration: (S)