کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1350758 | 980467 | 2006 | 6 صفحه PDF | دانلود رایگان |

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)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 5, 6 March 2006, Pages 750–755