| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350081 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
The expedient synthesis of enantiopure masked 1,2-amino alcohols (ee >99%) including their alkyl substituted analogues has been achieved by the regioselective ring opening of epoxides using phthalimide, followed by highly efficient kinetic resolution under mild and environmentally friendly conditions. The addition of co-solvents during kinetic resolution significantly improved the enantioselectivity with reduction in time.
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N-(2-Hydroxy)-butylphthalimideC12H13NO3Ee >99% (HPLC analysis)[α]D25=+18.4 (c 0.5, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
N-(2-Hydroxy)-pentylphthalimideC13H15NO3Ee >99% (HPLC analysis)[α]D25=+10.7 (c 1, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
N-(2-Hydroxy-2-phenyl)ethylphthalimideC16H13NO3Ee >99% (HPLC analysis)[α]D25=+23.2 (c 1, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
N-(2-Hydroxy)-octylphthalimideC16H21NO3Ee = 93.8% (HPLC analysis)[α]D25=+7.5 (c 1, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
N-(2-Hydroxy-3-phenoxy)propylphthalimideC17H15NO4Ee >99% (HPLC analysis)[α]D25=+23.2 (c 0.5, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-[2-Hydroxy-3-(p-methoxy-phenoxy)]propylphthalimideC18H17NO5Ee >99% (HPLC analysis)[α]D25=+25.5 (c 0.5, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy)-butylphthalimideC14H15NO4Ee >99% (HPLC analysis)[α]D25=+35.9 (c 1, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy)-pentylphthalimideC15H17NO4Ee >99% (HPLC analysis)[α]D25=+23.5 (c 1, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy-2-phenyl)ethylphthalimideC18H15NO4Ee >99% (HPLC analysis)[α]D25=-21.7 (c 1, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy)-octylphthalimideC18H23NO4Ee = 65.3% (HPLC analysis)[α]D25=+11.1 (c 1, CHCl3)Absolute configuration: (R)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy-3-phenoxy)propylphthalimideC19H17NO5Ee = 51% (HPLC analysis)[α]D25=-10.5 (c 1, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
N-(2-Acetoxy-3-(p-methoxy-phenoxy)propylphthalimideC20H19NO6Ee = 99% (HPLC analysis)[α]D25=-14.4 (c 0.5, CHCl3)Absolute configuration: (S)Source of chirality: enzymatic hydrolysis
