| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346066 | Tetrahedron: Asymmetry | 2012 | 10 Pages |
The transition metal-catalyzed asymmetric variant of the title reaction is normally limited to N-protected isatins. However, Rh(I)/chiral sulfoxide phosphine complexes were found to catalyze the enantioselective addition of arylboronic acids to NH isatins under mild conditions. A variety of chiral 3-aryl-3-hydroxyl-2-oxindoles were obtained with high yields and with good to excellent enantioselectivities (85–92% ee).
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(R)-1-Benzyl-3-hydroxy-3-phenylindolin-2-oneC21H17NO2[α]D20=+37 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-Hydroxy-1-methyl-3-phenylindolin-2-oneC15H13NO2[α]D20=+65 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-Hydroxy-1-(4-nitrobenzyl)-3-phenylindolin-2-oneC21H16N2O4[α]D20=+19 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
3-Hydroxy-1-(4-methoxybenzyl)-3-phenylindolin-2-oneC22H19NO3[α]D20=+22 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-Hydroxy-3-phenylindolin-2-oneC14H11NO2[α]D20=-10 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-phenylindolin-2-oneC14H10ClNO2[α]D20=-68 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Fluoro-3-hydroxy-3-phenylindolin-2-oneC14H10FNO2[α]D20=+7 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-Hydroxy-5-methyl-3-phenylindolin-2-oneC15H13NO2[α]D20=-50 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-o-tolylindolin-2-oneC15H12ClNO2[α]D20=+28 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-m-tolylindolin-2-oneC15H12ClNO2[α]D20=-67 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-(3-methoxyphenyl)indolin-2-oneC15H12ClNO3[α]D20=-55 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-oneC15H12ClNO3[α]D20=-116 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphine Absolute configuration: (R)
(R)-5-Chloro-3-(4-fluorophenyl)-3-hydroxyindolin-2-oneC14H9ClFNO2[α]D20=-80 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-hydroxy-3-p-tolylindolin-2-oneC15H12ClNO2[α]D20=-86 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-(4-tert-Butylphenyl)-5-chloro-3-hydroxyindolin-2-oneC18H18ClNO2[α]D20=-82 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-3-(4-(Benzyloxy)phenyl)-5-chloro-3-hydroxyindolin-2-oneC21H16ClNO3[α]D20=-83 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-5-Chloro-3-(3,5-dimethylphenyl)-3-hydroxyindolin-2-oneC16H14ClNO2[α]D20=-75 (c 0.1, MeOH)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-phenylindolin-2-oneC21H16ClNO2[α]D20=+6 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-fluoro-3-hydroxy-3-phenylindolin-2-oneC21H16FNO2[α]D20=+57 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-3-hydroxy-5-methyl-3-phenylindolin-2-oneC22H19NO2[α]D20=+17 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-o-tolylindolin-2-oneC22H18ClNO2[α]D20=+98 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-m-tolylindolin-2-oneC22H18ClNO2[α]D20=+9 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-(3-methoxyphenyl)indolin-2-oneC22H18ClNO3[α]D20=+16 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-oneC22H18ClNO3[α]D20=-43 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-(4-fluorophenyl)-3-hydroxyindolin-2-oneC21H15ClFNO2[α]D20=-13 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-hydroxy-3-p-tolylindolin-2-oneC22H18ClNO2[α]D20=-22 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-3-(4-tert-butylphenyl)-5-chloro-3-hydroxyindolin-2-oneC25H24ClNO2[α]D20=-23 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-3-(4-(benzyloxy)phenyl)-5-chloro-3-hydroxyindolin-2-oneC28H22ClNO3[α]D20=-45 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
(R)-1-Benzyl-5-chloro-3-(3,5-dimethylphenyl)-3-hydroxyindolin-2-oneC23H20ClNO2[α]D20=+13 (c 0.1, CHCl3)Source of chirality: (R)-(6-(tert-butylsulfinyl)-2,3-dimethoxyphenyl)diphenylphosphineAbsolute configuration: (R)
