کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1345127 980181 2016 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Asymmetric Henry reaction catalyzed by Cu(II)-based chiral amino alcohol complexes with C2-symmetry
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Asymmetric Henry reaction catalyzed by Cu(II)-based chiral amino alcohol complexes with C2-symmetry
چکیده انگلیسی

A series of chiral amino alcohol ligands was prepared using commercial amino alcohols and phthalaldehydes. These ligands were used as catalysts in asymmetric Henry reactions in the presence of Cu(II) ions giving good yields (up to 97%) and enantiomeric excesses (ee, up to 98%). The DFT calculations showed the effect of the trans/cis configurations of the Cu-complexes on the origin of enantioselectivity. The easy catalyst preparation, mild reaction conditions, high yields and excellent enantioselectivities make these catalysts suitable for widespread use.

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(S)-(−)-2-Benzylamino-3-phenylpropan-1-olC16H19NO[α]D25 = −23.8 (c 1.06, CH2Cl2)Absolute configuration: (S)

(S)-(−)-2-Phenylamino-2-phenylethan-1-olC15H17NO[α]D25 = −26.2 (c 1.14, CH2Cl2)Absolute configuration: (S)

(−)-N,N′-Bis[(2S)-1-hydroxy-3-phenylpropan-2-yl]-1,4-xylylenediamineC26H32N2O2[α]D25 = −48.7 (c 1.44, CH2Cl2)Absolute configuration: (S)

(−)-N,N′-Bis[(1S)-2-hydroxy-1-phenylethyl]-1,4-xylylenediamineC24H28N2O2[α]D25 = −51.6 (c 1.38, CH2Cl2)Absolute configuration: (S)

(−)-N,N′-Bis[(2S)-1-hydroxy-3-phenylpropan-2-yl]-1,3-xylylenediamineC26H32N2O2[α]D25 = −44.2 (c 1.33, CH2Cl2)Absolute configuration: (S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 27, Issue 16, 1 September 2016, Pages 732–739
نویسندگان
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