| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346560 | Tetrahedron: Asymmetry | 2011 | 8 Pages |
The synthesis and utility of novel indole-olefin-oxazoline (IndOlefOx)-ligands are described. The use of these ligands was demonstrated in rhodium catalyzed asymmetric conjugate additions between 2-cyclopentenone, 2-cyclohexenone, and 2-cycloheptenone with different boron reagents with good yields and enantioselectivities of up to 94%.
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(S,E)-4-Benzyl-2-(1-methyl-3-styryl-1H-indol-2-yl)-4,5-dihydrooxazoleC29H29N2O3[α]D20=-47.3 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-4-Benzyl-2-(3-(3,4-dimethoxystyryl)-1-methyl-1H-indol-2-yl)-4,5-dihydrooxazoleC29H29N2O3[α]D20=-35.5 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-4-Benzyl-2-(3-(3,4-dimethoxystyryl)-1-(methoxymethyl)-1H-indol-2-yl)-4,5-dihydrooxazoleC30H30N2O4[α]D20=-26.0 (c 1.3, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-2-(3-(3,4-Dimethoxystyryl)-1-methyl-1H-indol-2-yl)-4-isopropyl-4,5-dihydrooxazoleC25H29N2O3[α]D20=-46.5 (c 0.6, CDCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-2-(3-(3,4-Dimethoxystyryl)-1-(methoxymethyl)-1H-indol-2-yl)-4-isopropyl-4,5-dihydrooxazoleC26H30N2O4[α]D20=-43.1 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-4-Benzyl-2-(3-(2,5-dimethoxystyryl)-1-methyl-1H-indol-2-yl)-4,5-dihydrooxazoleC29H29N2O3[α]D20=-36.6 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S)-2-(3-(3,4-Dimethoxyphenethyl)-1-methyl-1H-indol-2-yl)-4-isopropyl-4,5-dihydrooxazoleC25H29N2O3[α]D20=-37.7 (c 0.6, CDCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-N-(1-Hydroxy-3-phenylpropan-2-yl)-1-methyl-3-styryl-1H-indole-2-carboxamideC27H26N2O2[α]D20=-65.7 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-3-(3,4-Dimethoxystyryl)-N-(1-hydroxy-3-phenylpropan-2-yl)-1-methyl-1H-indole-2-carboxamideC29H30N2O4[α]D20=-77.6 (c 0.5, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-3-(3,4-Dimethoxystyryl)-N-(1-hydroxy-3-phenylpropan-2-yl)-1-(methoxymethyl)-1H-indole-2-carboxamideC30H32N2O5[α]D20=-77.6 (c 0.5, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-3-(3,4-Dimethoxystyryl)-N-(1-hydroxy-3-methylbutan-2-yl)-1-methyl-1H-indole-2-carboxamideC25H30N2O4[α]D20=-14.4 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-3-(3,4-Dimethoxystyryl)-N-(1-hydroxy-3-methylbutan-2-yl)-1-(methoxymethyl)-1H-indole-2-carboxamideC26H32N2O5[α]D20=-10.5 (c 1.0, CHCl3)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S,E)-3-(2,5-Dimethoxystyryl)-N-(1-hydroxy-3-phenylpropan-2-yl)-1-methyl-1H-indole-2-carboxamideC29H30N2O4[α]D20=-124.6 (c 0.5, DMF)Source of chirality: l-phenylalaninolAbsolute configuration: (S)
(S)-3-PhenylcycloheptanoneC13H16Oee 75%[α]D20=-43.0 (c 0.5, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (S)
(S)-3-PhenylcyclopentanoneC11H12Oee 91%[α]D20=-79.2 (c 1.0, CHCl3)Source of chirality: asymmetric conjugate additionAbsolute configuration: (S)
