| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345178 | Tetrahedron: Asymmetry | 2007 | 12 Pages |
An enantiodivergent preparation of (+)-(R)- and (−)-(S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-one, (R)- and (S)-9, and several derivatives, from 4,4-dimethyl-1-phenylpyrrolidin-2,3-dione, 4, and (R)- or (S)-1-phenylethylamine, (R)- or (S)-5, as the chirality transfer agents, is described. Amine (S)-9 has also been used as a chiral auxiliary in a diastereoselective Michael reaction.
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(R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)imino]pyrrolidin-2-oneC20H22N2OEe = ⩾97%[α]D20=+159 (c 0.57, CH2Cl2)Source of chirality: (R)-1-phenylethylamineAbsolute configuration: (R)
(3S,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)amino]pyrrolidin-2-oneC20H24N2OEe = ⩾97%[α]D25=-57.2 (c 1.2, CH2Cl2)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3S,1′R)
(3S,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)amino]pyrrolidin-2-one monomaleateC20H24N2O·C4H4O4Ee = ⩾97%[α]D20=-21 (c 0.61, EtOH)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3S,1′R)
(3R,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)amino]pyrrolidin-2-oneC20H24N2OEe = ⩾97%[α]D25=+128 (c 1.3, CH2Cl2)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3R,1′R)
(3R,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)amino]pyrrolidin-2-one hydrochlorideC20H24N2O·HClEe = ⩾97%[α]D20=+126 (c 0.51, MeOH)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3R,1′R)
(S)-3-Amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneC12H16N2OEe = ⩾97%[α]D24=-24.5 (c 1.1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-4,4-dimethyl-1-phenylpyrrolidin-2-one p-nitrobenzoateC12H16N2O·C7H5NO4Ee = ⩾97%[α]D25=-15 (c 0.51, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-4,4-dimethyl-1-phenylpyrrolidin-2-one mono-O,O-di-p-toluoyl-l-tartrateC12H16N2O·C20H18O8Ee = ⩾97%[α]D24=-99.8 (c 1.17, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-(Dimethylamino)-4,4-dimethyl-1-phenylpyrrolidin-2-oneC14H20N2OEe = ⩾97%[α]D20=-35 (c 0.61, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S)
(S)-4,4-Dimethyl-1-phenyl-3-(p-toluenesulfonylamino)pyrrolidin-2-oneC19H22N2O3SEe = ⩾97%[α]D20=-6 (c 0.51, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S)
(3S,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)methylamino]pyrrolidin-2-oneC21H26N2OEe = ⩾97%[α]D25=-74.8 (c 1.1, CH2Cl2)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3S,1′R)
(3S,1′R)-4,4-Dimethyl-1-phenyl-3-[(1-phenylethyl)methylamino]pyrrolidin-2-one monomaleateC21H26N2O·C4H4O4Ee = ⩾97%[α]D20=-24 (c 0.55, CH2Cl2)Source of chirality: asymmetric synthesis and (R)-1-phenylethylamineAbsolute configuration: (3S,1′R)
(S)-4,4-Dimethyl-3-methylamino-1-phenylpyrrolidin-2-oneC13H18N2OEe = ⩾97%[α]D20=-35 (c 0.59, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-[(4,4-Dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)imino]-4,4-dimethyl-1-phenylpyrrolidin-2-oneC24H27N3O2Ee = ⩾97%[α]D25=-187 (c 0.50, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S)
(S,S)-Bis(4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)amineC24H29N3O2Ee = ⩾97%[α]D25=-53 (c 0.51, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S,S)
(S,S)-2,6-Bis[(4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)aminomethyl]pyridineC31H37N5O2Ee = ⩾97%[α]D22=-41.2 (c 0.45, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S,S)
(S,S)-2,6-Bis[(4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)aminomethyl]pyridine dihydrochlorideC31H37N5O2·2HClEe = ⩾97%[α]D22=-87.2 (c 0.51, MeOH)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S,S)
Ethyl 2-{(S)-[(4,4-dimethyl-2-oxo-1-phenylpyrrolidin-3-yl)amino]}cyclohex-1-enecarboxylateC21H28N2O3Ee = ⩾97%[α]D25=+56.9 (c 0.65, CH2Cl2)Source of chirality: (S)-3-amino-4,4-dimethyl-1-phenylpyrrolidin-2-oneAbsolute configuration: (S)
