Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1349043 | Tetrahedron: Asymmetry | 2010 | 15 Pages |
Kinetic resolution of β-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21.
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Dimethyl (R)-(2-hydroxy-2-phenylethyl)phosphonateC10H15O4PEe = 49%[α]D20=-14.5 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonateC17H19O5PEe = 62%[α]D20=-10.6 (c 0.53, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-phenyl-2-(2-toluoyloxy)ethyl]phosphonateC18H21O5PEe = 69%[α]D20=+3.7 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2-methoxybenzoyloxy)-2-phenylethyl]phosphonateC18H21O6PEe = 6%[α]D20=-0.15 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-phenylethyl]phosphonateC17H18FO5PEe = 80%[α]D20=-6.5 (c 0.69, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(3-fluorobenzoyloxy)-2-phenylethyl]phosphonateC17H18FO5PEe = 59%[α]D20=-7.9 (c 0.70, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(4-fluorobenzoyloxy)-2-phenylethyl]phosphonateC17H18FO5PEe = 52%[α]D20=-6.6 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2,6-difluorobenzoyloxy)-2-phenylethyl]phosphonateC17H17F2O5PEe = 56%[α]D20=+7.1 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-(2-pentafluorobenzoyloxy-2-phenylethyl)phosphonateC17H14F5O5PEe = 47%[α]D20=+3.4 (c 0.96, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2-chlorobenzoyloxy)-2-phenylethyl]phosphonateC17H18ClO5PEe = 72%[α]D20=+4.1 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2-bromobenzoyloxy)-2-phenylethyl]phosphonateC17H18BrO5PEe = 61%[α]D20=-6.2 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(1-naphthoyloxy)-2-phenylethyl]phosphonateC21H21O5PEe = 64%[α]D20=+28.7 (c 0.40, acetone)Source of chirality: catalytic kinetic resolution
Dimethyl (S)-[2-(2-naphthoyloxy)-2-phenylethyl]phosphonateC21H21O5PEe = 55%[α]D20=-37.3 (c 0.51, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-(2-acetoxy-2-phenylethyl)phosphonateC12H17O5PEe = 16%[α]D20=+2.6 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-(2-chloroacetoxy-2-phenylethyl)phosphonateC12H16ClO5PEe = 8%[α]D20=+4.7 (c 0.93, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-(2-phenyl-2-phenylaminocarbonyloxyethyl)phosphonateC17H20NO5PEe = 29%[α]D20=-6.7 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (R)-(2-hydroxy-2-phenylethyl)phosphonateC12H19O4PEe = 41%[α]D20=-10.8 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonateC19H23O5PEe = 66%[α]D20=-7.8 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diethyl (S)-[2-(2-fluorobenzoyloxy)-2-phenylethyl]phosphonateC19H22FO5PEe = 83%[α]D20=+2.0 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diisopropyl (R)-(2-hydroxy-2-phenylethyl)phosphonateC14H23O4PEe = 36%[α]D20=-10.1 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diisopropyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonateC21H27O5PEe = 66%[α]D20=-11.6 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diisopropyl (S)-[2-(2-fluorobenzoyloxy)-2-phenylethyl]phosphonateC21H26FO5PEe = 77%[α]D20=+2.9 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dibutyl (R)-(2-hydroxy-2-phenylethyl)phosphonateC16H27O4PEe = 20%[α]D20=-11.7 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dibutyl (S)-(2-benzoyloxy-2-phenylethyl)phosphonateC23H31O5PEe = 56%[α]D20=-7.8 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dibutyl (S)-[2-(2-fluorobenzoyloxy)-2-phenylethyl]phosphonateC23H30FO5PEe = 82%[α]D20=-2.7 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(2-methylphenyl)ethyl]phosphonateC11H17O4PEe = 34%[α]D20=-18.8 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(2-methylphenyl)ethyl]phosphonateC18H20FO5PEe = 87%[α]D20=-27.0 (c 0.83, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(3-methylphenyl)ethyl]phosphonateC11H17O4PEe = 31%[α]D20=-11.3 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(3-methylphenyl)ethyl]phosphonateC18H20FO5PEe = 83%[α]D20=+9.2 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-methylphenyl)ethyl]phosphonateC11H17O4PEe = 38%[α]D20=-12.5 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(4-methylphenyl)ethyl]phosphonateC18H20FO5PEe = 75%[α]D20=+2.8 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(2-methoxyphenyl)ethyl]phosphonateC11H17O5PEe = 38%[α]D20=-20.4 (c 3.5, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(2-methoxyphenyl)ethyl]phosphonateC18H20FO6PEe = 74%[α]D20=-17.4 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-methoxyphenyl)ethyl]phosphonateC11H17O5PEe = 29%[α]D20=-7.1 (c 3.8, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(4-methoxyphenyl)ethyl]phosphonateC18H20FO6PEe = 84%[α]D20=+1.7 (c 1.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-nitrophenyl)ethyl]phosphonateC10H14NO6PEe = 29%[α]D20=-7.6 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(4-nitrophenyl)ethyl]phosphonateC17H17FNO7PEe = 57%[α]D20=-2.3 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-fluorophenyl)ethyl]phosphonateC10H14FO4PEe = 41%[α]D20=-12.3 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(4-fluorophenyl)ethyl]phosphonateC17H17F2O5PEe = 72%[α]D20=+2.1 (c 2.4, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-chlorophenyl)ethyl]phosphonateC10H14ClO4PEe = 37%[α]D20=-9.2 (c 1.8, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(4-chlorophenyl)-2-(2-fluorobenzoyloxy)ethyl]phosphonateC17H17ClFO5PEe = 66%[α]D20=-9.0 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(4-bromophenyl)ethyl]phosphonateC10H14BrO4PEe = 49%[α]D20=-11.5 (c 0.68, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(4-bromophenyl)-2-(2-fluorobenzoyloxy)ethyl]phosphonateC17H17BrFO5PEe = 60%[α]D20=-9.6 (c 1.3, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(1-naphthyl)ethyl]phosphonateC14H17O4PEe = 43%[α]D20=-27.6 (c 2.6, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(1-naphthyl)ethyl]phosphonateC21H20FO5PEe = 79%[α]D20=-60.0 (c 2.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-[2-hydroxy-2-(2-naphthyl)ethyl]phosphonateC14H17O4PEe = 47%[α]D20=-14.3 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-2-(2-naphthyl)ethyl]phosphonateC21H20FO5PEe = 72%[α]D20=-24.6 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-(2-hydroxypropyl)phosphonateC5H13O4PEe = 10%[α]D20=-1.4 (c 0.46, CHCl3)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)propyl]phosphonateC12H16FO5PEe = 57%[α]D20=+15.2 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (E)-(R)-(2-hydroxy-4-phenylbut-3-enyl)phosphonateC12H17O4PEe = 38%[α]D20=+3.0 (c 1.2, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Dimethyl (E)-(S)-[2-(2-fluorobenzoyloxy)-4-phenylbut-3-enyl]phosphonateC19H20FO5PEe = 58%[α]D20=-13.3 (c 0.80, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (R)-(2-hydroxy-4-phenylbut-3-ynyl)phosphonateC12H15O4PEe = 50%[α]D20=+3.4 (c 0.99, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Dimethyl (S)-[2-(2-fluorobenzoyloxy)-4-phenylbut-3-ynyl]phosphonateC19H18FO5PEe = 47%[α]D20=+4.6 (c 0.59, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diethyl (R)-[2-hydroxy-2-(2-methylphenyl)ethyl]phosphonateC13H21O4PEe = 60%[α]D20=-25.8 (c 0.91, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (S)-[2-(2-fluorobenzoyloxy)-2-(2-methylphenyl)ethyl]phosphonateC20H24FO5PEe = 78%[α]D20=-24.1 (c 1.1, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diethyl (R)-[2-hydroxy-2-(4-methoxyphenyl)ethyl]phosphonateC13H21O5PEe = 59%[α]D20=-12.4 (c 1.6, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (S)-[2-(2-fluorobenzoyloxy)-2-(4-methoxyphenyl)ethyl]phosphonateC20H24FO6PEe = 77%[α]D20=+0.95 (c 0.96, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diethyl (R)-[2-hydroxy-2-(1-naphthyl)ethyl]phosphonateC16H21O4PEe = 47%[α]D20=-31.5 (c 0.76, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (S)-[2-(2-fluorobenzoyloxy)-2-(1-naphthyl)ethyl]phosphonateC23H24FO5PEe = 61%[α]D20=-44.9 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)
Diethyl (R)-(2-hydroxypropyl)phosphonateC7H17O4PEe = 49%[α]D20=-5.2 (c 0.87, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (R)
Diethyl (S)-[2-(2-fluorobenzoyloxy)propyl]phosphonateC14H20FO5PEe = 56%[α]D20=+15.1 (c 1.0, acetone)Source of chirality: catalytic kinetic resolutionAbsolute configuration: (S)