کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350758 980467 2006 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones
چکیده انگلیسی

An operationally simple and mild protocol for the catalytic enantioselective epoxidation of enones has been established using a series of chiral pyrrolidinylmethanol-based dendritic catalysts and tert-butyl hydroperoxide (TBHP) as an oxidant. The epoxides have been obtained in good yields and ee up to 78%.

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(2R,3S)-Phenyl(-3-phenyloxiran-2-yl)methanoneC15H12O2Ee = 74%[α]D23=-116.3 (c 0.40, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

((2R,3S)-3-(4-Chlorophenyl)oxiran-2-yl)(phenyl)methanoneC15H11ClO2Ee = 73%[α]D23=-164.9 (c 0.40, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

(2R,3S)-(4-Chlorophenyl)(-3-phenyloxiran-2-yl)methanoneC15H11ClO2Ee = 73%[α]D23=-66.8 (c 0.65, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

(2R,3S)-(4-Fluorophenyl)(-3-phenyloxiran-2-yl)methanoneC15H11FO2Ee = 74%[α]D23=-92.5 (c 0.90, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

(2R,3S)-(4-Nitrophenyl)(-3-phenyloxiran-2-yl)methanoneC15H11NO4Ee = 73%[α]D23=-99.6 (c 1.00, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

(2R,3S)-Biphenyl-4-yl(-3-phenyloxiran-2-yl)methanoneC21H16O2Ee = 77%[α]D23=-85.6 (c 0.56, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

((2R,3S)-3-(4-Chlorophenyl)oxiran-2-yl)(4-fluorophenyl)methanoneC15H10ClFO2Ee = 78%[α]D23=-66.8 (c 0.65, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

((2R,3S)-3-(2-Chlorophenyl)oxiran-2-yl)(phenyl)methanoneC15H11ClO2Ee = 56%[α]D23=-105.8 (c 1.00, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

1-((2R,3S)-3-Phenyloxiran-2-yl)ethanoneC10H10O2Ee = 69%[α]D23=-77.6 (c 1.00, CHCl3)Source of chirality: asymmetric oxidationAbsolute configuration: (2R,3S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 5, 6 March 2006, Pages 750–755
نویسندگان
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