One-pot asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones catalyzed by amino acid-derived sulfonamides

An organocatalyzed approach to the asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones using amino-acid derived sulfonamides as organocatalysts, which can be easily prepared starting from l-proline, l-alanine, and l-phenylalanine, has been developed in high yields (up to 92%) and with moderate to good enantioselectivities (up to 74% ee). Additionally, opposite enantioselectivities for primary and secondary amino acid sulfonamides have also been observed.

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N-2,4,6-Tris-(methylbenzene)sulfoneyl-l-proline amideC14H20N2O3S[α]D25=+67.7 (c 1, CHCl3)Source of chirality: Chiral poolAbsolute configuration: (S)

N-2,4,6-Tris-(methylbenzene)sulfoneyl-l-alanine amideC12H18N2O3S[α]D25=-34.5 (c 1, MeOH)Source of chirality: Chiral poolAbsolute configuration: (S)

N-2,4,6-Tris-(isopropylbenzene)sulfoneyl-l-alanine amideC18H30N2O3S[α]D25=-25.2 (c 1, MeOH)Source of chirality: Chiral poolAbsolute configuration: (S)

N-4-Dodecylbenzenesulfoneyl-l-alanine amideC21H36N2O3S[α]D25=-77.4 (c 1, CHCl3)Source of chirality: Chiral poolAbsolute configuration: (S)

N-2,4,6-Tris-(methylbenzene)sulfoneyl-l-phenylalanine amideC18H22N2O3S[α]D25=-64.4 (c 1, MeOH)Source of chirality: Chiral poolAbsolute configuration: (S)

N-2,4,6-Tris-(isopropylbenzene)sulfoneyl-l-phenylalanine amideC12H34N2O3S[α]D25=-46.2 (c 1, MeOH)Source of chirality: Chiral poolAbsolute configuration: (S)

N-4-Dodecylbenzenesulfoneyl-l-phenylalanine amideC27H40N2O3S[α]D25=-98.2 (c 1, MeOH)Source of chirality: Chiral poolAbsolute configuration: (S)

2-Phenyl-2,3dihydroquinolin-4-(1H)-oneC15H13NO[α]D25=-19.4 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(2-Hydroxypheneyl)-2,3-dihydroquinolin-4(1H)-oneC15H13NO2[α]D25=-31.8 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(4-Hydroxypheneyl)-2,3-dihydroquinolin-4(1H)-oneC15H13NO2[α]D25=-23.1 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(4-Bromopheneyl)-2,3-dihydroquinolin-4(1H)-oneC15H12BrNO[α]D25=-17.4 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(3-Methoxypheneyl)-2,3-dihydroquinolin-4(1H)-oneC16H15NO2[α]D25=-23.2 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(3-Chloropheneyl)-2,3-dihydroquinolin-4(1H)-oneC15H12CINO[α]D25=-15.4 (c0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(4-(Dimethylamino)pheneyl)-2,3-dihydroquinolin-4(1H)-oneC17H18N2O[α]D25=-19.3 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(4-Nitropheneyl)-2,3-dihydroquinolin-4(1H)-oneC15H12N2O3[α]D25=-19.4 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(Isobutyl)-2,3-dihydroquinolin-4(1H)-oneC13H17NO[α]D25=-25.2 (c0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(Pyridin-2-yl)-2,3-dihydroquinolin-4(1H)-oneC14H12N2O[α]D25=-19.6 (c 0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)

2-(4-(1H-Indol-3-yl)phenyl)-2,3-dihydroquinolin-4(1H)-oneC17H14N2O[α]D25=-11.2 (c0.5, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (R)