کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1350081 | 980422 | 2008 | 6 صفحه PDF | دانلود رایگان |

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
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 16, 22 August 2008, Pages 1898–1903