| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346901 | Tetrahedron: Asymmetry | 2011 | 9 Pages |
Axially chiral BINIM–Ni(II) complexes are effective catalysts in the asymmetric chlorination of 3-substituted oxindoles and give the corresponding chlorinated adducts in good yields and up to 88% ee.
Graphical abstractAxially chiral BINIM–Ni(II) complexes are effective catalysts in the asymmetric chlorination of 3-substituted oxindoles to give the corresponding chlorinated adducts in good yields and up to 88% ee value.Figure optionsDownload full-size imageDownload as PowerPoint slide
(R)-tert-Butyl 3-chloro-2-oxo-3-phenylindoline-1-carboxylateC19H18ClNO3Ee = 85%[α]D20=-124 (c 0.05, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-methyl-2-oxo-3-phenylindoline-1-carboxylateC20H20ClNO3Ee = 67%[α]D20=-77.7 (c 1.0, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-fluoro-2-oxo-3-phenylindoline-1-carboxylateC19H17ClFNO3Ee = 88%[α]D20=-96.7 (c 1.7, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-methoxy-2-oxo-3-phenylindoline-1-carboxylateC20H20ClNO4Ee = 82%[α]D20=-101.3 (c 1.35, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylateC19H17ClNO3Ee = 74%[α]D20=-107.9 (c 1.5, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-3-(4-fluorophenyl)-5-methyl-2-oxoindoline-1-carboxylateC20H19ClFNO3Ee = 60%[α]D20=-87.0 (c 1.6, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-fluoro-3-(4-fluorophenyl)-2-oxoindoline-1-carboxylateC19H16ClF2NO4Ee = 75%[α]D20=-63.3 (c 1.6, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-3-(4-fluorophenyl)-5-methoxy-2-oxoindoline-1-carboxylateC20H19ClFNO4Ee = 72%[α]D20=-106.9 (c 1.65, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-fluoro-2-oxo-3-(p-tolyl)indoline-1-carboxylateC20H19ClFNO3Ee = 85%[α]D20=-87.0 (c 1.45, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-2-oxo-3-(m-tolyl)indoline-1-carboxylateC20H20ClNO3Ee = 72%[α]D20=-2.2 (c 1.5, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-3-(naphthalen-2-yl)-2-oxoindoline-1-carboxylateC23H20ClNO3Ee = 52%[α]D20=-45.9 (c 1.5, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-3-methyl-2-oxoindoline-1-carboxylateC14H16ClNO3Ee = 20%[α]D20=-15.6 (c 1.2, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-methoxy-2-oxo-3-(p-tolyl)indoline-1-carboxylateC21H22ClNO4Ee = 15%[α]D20=-14.9 (c 1.5, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-2-oxo-3-(p-tolyl)indoline-1-carboxylateC20H20ClNO3Ee = 7%[α]D20=-4.2 (c 1.5, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
(R)-tert-Butyl 3-chloro-5-methyl-2-oxo-3-(p-tolyl)indoline-1-carboxylateC21H22ClNO3Ee = 7%[α]D20=-4.6 (c 0.7, CHCl3)Source of chirality: asymmetric catalysisAbsolute configuration: (R)
