کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350081 980422 2008 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
An expedient chemo-enzymatic method for the synthesis of optically active masked 1,2-amino alcohols
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
An expedient chemo-enzymatic method for the synthesis of optically active masked 1,2-amino alcohols
چکیده انگلیسی

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.

Figure optionsDownload as PowerPoint slide

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

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 19, Issue 16, 22 August 2008, Pages 1898–1903
نویسندگان
, , , , , , ,