| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347856 | Tetrahedron: Asymmetry | 2008 | 7 Pages |
Kinetic resolution of phosphoryl and sulfonyl esters of 1,1′-bi-2-naphthol has been achieved via the Pd-catalyzed alcoholysis of their vinyl ethers. The highest krel value reached 36.8 with substrate 3c, and (R)-3c 99.0% ee was obtained in 43% isolated yield.
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Dimethyl 2′-vinyloxy-1,1′-binaphthyl-2-yl phosphateC24H21O5PEe = 94.8%[α]D23=+29.5 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
Diethyl 2′-vinyloxy-1,1′-binaphthyl-2-yl phosphateC26H25O5PEe = 98.5%[α]D28=+39.6 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
2-(5,5-Dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yloxy)-2′-vinyloxy-1,1′-binaphthaleneC27H25O5PEe = 41.0%[α]D28=+2.7 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
2′-Vinyloxy-1,1′-binaphthyl-2-yl dicyclohexylphosphinateC34H37O3PEe = 27.4%[α]D28=-0.6 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
Dimethyl 2′-hydroxy-1,1′-binaphthyl-2-yl phosphateC22H19O5PEe = 73.0%[α]D24=-25.2 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
Diethyl 2′-hydroxy-1,1′-binaphthyl-2-yl phosphateC24H23O5PEe = 62.7%[α]D25=-32.2 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2-(5,5-Dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yloxy)-2′-hydroxy-1,1′-binaphthaleneC25H23O5PEe = 63.8%[α]D25=-8.5 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2′-Hydroxy-1,1′-binaphthyl-2-yl dicyclohexylphosphinateC32H35O3PEe = 55.2%[α]D25=-26.9 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2′-Vinyloxy-1,1′-binaphthyl-2-yl methanesulfonateC23H18O4SEe = 40.7%[α]D28=-4.4 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
2′-Vinyloxy-1,1′-binaphthyl-2-yl 4-toluenesulfonateC29H22O4SEe = 45.6%[α]D28=+4.26 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
2′-Vinyloxy-1,1′-binaphthyl-2-yl 2,4,6-triisopropylbenzenesulfonateC37H38O4SEe = 99.0%[α]D23=+28.0 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
(aR,R)-2′-Vinyloxy-1,1′-binaphthyl-2-yl camphorsulfonateC32H30O5SDe = 54.8%[α]D23=-11.8 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (aR,R)
(aR,S)-2′-Vinyloxy-1,1′-binaphthyl-2-yl camphorsulfonateC32H30O5SDe = 95.0%[α]D23=-2.9 (c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (aR,S)
2′-Hydroxy-1,1′-binaphthyl-2-yl methanesulfonateC21H16O4SEe = 46.7%[α]D24=-13.7 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2′-Hydroxy-1,1′-binaphthyl-2-yl 4-toluenesulfonateC27H20O4SEe = 51.4%[α]D25=-25.9 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2′-Hydroxy-1,1′-binaphthyl-2-yl 2,4,6-triisopropylbenzenesulfonateC35H36O4SEe = 75.7%[α]D23=-54.6 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
(aS,R)-2′-Hydroxy-1,1′-binaphthyl-2-yl camphorsulfonateC30H28O5SDe = 59.5%[α]D23=-22.1 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (aS,R)
(aS,S)-2′-Hydroxy-1,1′-binaphthyl-2-yl camphorsulfonateC30H28O5SDe = 58.9%[α]D23=-36.0 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (aS,S)
Dimethyl 2′-vinyloxy-(5,5′,6,6′-tetramethyl-1,1′-biphenyl)-2-yl phosphateC20H25O5PEe = 98.1%[α]D24=+21.6 (c 2.30, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
2′-Vinyloxy-(5,5′,6,6′-tetramethyl-1,1′-biphenyl)-2-yl 2,4,6-triisopropylbenzenesulfonateC33H42O4SEe = 66.9%[α]D24=-28.7(c 1.00, C6H6)Source of chirality: kinetic resolutionAbsolute configuration: (R)
Dimethyl 2′-hydroxy-(5,5′,6,6′-tetramethyl-1,1′-biphenyl)-2-yl phosphateC18H23O5PEe = 56.6%[α]D25=-18.4 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
2′-Hydroxy-5,5′,6,6′-tetramethyl-1,1′-biphenyl-2-yl 2,4,6-triisopropylbenzenesulfonateC31H40O4SEe = 83.0%[α]D24=-48.3 (c 1.00, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S)
