| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348726 | Tetrahedron: Asymmetry | 2010 | 9 Pages |
Two classes of indole-phosphine oxazoline ligands have been prepared from readily available starting materials in good overall yields. These modular ligands include an indole skeleton with either a phosphine moiety or an oxazoline ring at the 2- or 3-position, respectively. The utility of these ligands was demonstrated in a catalytic asymmetric reaction: the palladium-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate was performed with enantioselectivities as high as 98%.
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(S)-N-(1-Hydroxy-3-methylbutan-2-yl)-1H-indole-2-carboxamideC14H18N2O2[α]D20=-46.3 (c 1.0, MeOH)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1H-indoleC14H16N2O[α]D20=+52.0 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC15H18N2O[α]D20=-55.8 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC16H20N2O2[α]D20=-37.3 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Diphenylphosphoryl)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H27N2O2P[α]D20=-88.9 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Diphenylphosphoryl)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC28H29N2O3P[α]D20=-79.5 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Diphenylphosphino)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H27N2OP[α]D20=-59.4 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Diphenylphosphino)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC28H29N2O2P[α]D20=-53.1 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-Bromo-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1H-indoleC14H15BrN2O[α]D20=+60.4 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-Bromo-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC15H17BrN2O[α]D20=-59.9 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-Bromo-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC16H19BrN2O2[α]D20=-46.0 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Dicyclohexylphosphino)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H39N2OP[α]D20=-36.5 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(Dicyclohexylphosphino)-2-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC28H41N2O2P[α]D20=-33.8 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-N-(1-Hydroxy-3-methylbutan-2-yl)-1H-indole-3-carboxamideC14H18N2O2[α]D20=-37.8 (c 1.0, MeOH)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1H-indoleC14H16N2O[α]D20=-29.7 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC15H18N2O[α]D20=-35.0 (c 0.8, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-3-(4-Isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC16H20N2O2[α]D20=-31.2 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(Dicyclohexylphosphino)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H39N2OP[α]D20=-21.0 (c 0.8, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(Dicyclohexylphosphino)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H39N2OP[α]D20=-21.0 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(Dicyclohexylphosphino)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC28H41N2O2P[α]D20=-20.1 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(Diphenylphosphino)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-methyl-1H-indoleC27H27N2OP[α]D20=-75.6 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
(S)-2-(Diphenylphosphino)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)-1-(methoxymethyl)-1H-indoleC28H29N2O2P[α]D20=-77.6 (c 1.0, DCM)Source of chirality: l-valinolAbsolute configuration: (S)
