| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347550 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
A conceptually new and efficient asymmetric synthesis of C-3 arylated or alkylated poly-substituted isoindolinones is reported. The key step is the diastereoselective reduction of an N-acylhydrazonium species derived from the previously assembled corresponding hydroxyl derivative bearing the (S)-2-methoxymethylpyrrolidine (SMP) auxiliary.
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2-Iodo-N-((S)-2-(2-methoxymethylpyrrolidin-1-yl)benzamideC13H17IN2O2Ee >96%[α]D21=-39.1 (c 0.79, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
2-Iodo-3,4,5-trimethoxy-N-((S)-2-(2-methoxymethylpyrrolidin-1-yl)benzamideC16H23IN2O5Ee >96%[α]D21=-44.3 (c 0.95, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
6-Iodo-1,3-benzodioxole-5-carboxylic acid ((S)-2-methoxymethylpyrrolidin-1-yl)amideC14H17IN2O4Ee >96%[α]D21=-35.8 (c 1.47, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
N-(2-Iodobenzoyl)-N-((S)-2-methoxymethylpyrrolidin-1-yl)benzamideC20H21IN2O3Ee >96%[α]D21=-88.2 (c 0.74, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
N-(2-Iodobenzoyl)-4-methoxy-N-((S)-2-methoxymethylpyrrolidin-1-yl)benzamideC21H23IN2O4Ee >96%[α]D21=-72.3 (c 1.77, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
N-(2-Iodo-3,4,5-trimethoxybenzoyl)-N-((S)-2-methoxymethylpyrrolidin-1-yl)benzamideC23H27IN2O6Ee >96%[α]D21=-81.1 (c 1.58, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
N-(6-Iodo-1,3-benzodioxole-5-carbonyl)-4-methoxy-N-((S)-2-methoxymethylpyrrolidin-1-yl)benzamideC22H23IN2O6Ee >96%[α]D21=-64.7 (c 1.98, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S)
(R)-2-((S)-2-Methoxymethylpyrrolidin-1-yl)-3-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-oneC21H24N2O3De >96%[α]D21=-37.1 (c 0.94, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S,3R)
(R)-2-((S)-2-Methoxymethylpyrrolidin-1-yl)-3-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-isoindol-1-oneC23H28N2O5De >96%[α]D21=-104.3 (c 0.83, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S,3R)
(R)-4,5,6-Trimethoxy-2-((S)-2-Methoxymethylpyrrolidin-1-yl)-3-phenyl-2,3-dihydro-1H-isoindol-1-oneC23H28N2O5De >96%[α]D21=-28.1 (c 1.21, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S,3R)
(R)-6-((S)-2-Methoxymethylpyrrolidin-1-yl)-7-(4-methoxyphenyl)-6,7-dihydro-1,3-dioxolo[4,5-f]-5H-isoindol-5-oneC22H24N2O5De >96%[α]D21=-1.6 (c 1.44, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (2S,7R)
(3R)-3-(4-Methoxyphenyl)-2,3-dihydro-1H-isoindol-1-oneC15H13NO2Ee >96%[α]D21=-115.5 (c 0.95, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (3R)
(R)-3-(3,4,5-Trimethoxyphenyl)-2,3-dihydro-1H-isoindol-1-oneC17H17NO4Ee >96%[α]D21=-139.9 (c 0.99, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (3R)
(R)-4,5,6-Trimethoxy-3-phenyl-2,3-dihydro-1H-isoindol-1-oneC17H17NO4Ee >96%[α]D21=-70.5 (c 0.92, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (3R)
(R)-7-Phenyl-6,7-dihydro-1,3-dioxolo[4,5-f]-5H-isoindol-5-oneC16H13NO4Ee >96%[α]D21=-34.1 (c 1.20, CHCl3)Source of chirality: (S)-prolineAbsolute configuration: (3R)
