کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1350775 980467 2006 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
An economic, practical access to enantiopure 1,1′-bi-2-naphthols: enantioselective complexation of threo-(1S,2S)-N-benzyl-N,N-dimethyl[1,3-dihydroxy-1-(4′-nitrophenyl)]-2-propylammonium chloride
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
An economic, practical access to enantiopure 1,1′-bi-2-naphthols: enantioselective complexation of threo-(1S,2S)-N-benzyl-N,N-dimethyl[1,3-dihydroxy-1-(4′-nitrophenyl)]-2-propylammonium chloride
چکیده انگلیسی

An economic, convenient access to enantiopure (R)- and (S)-1,1′-bi-2-naphthol (BINOL) has been discovered. Racemic 1,1′-bi-2-naphthol was reacted with threo-(1S,2S)-N-benzyl-N,N-dimethyl-[1,3-dihydroxyl-1-(4′-nitrophenyl)]-2-propylammonium chloride (BDDNPAC) in water-containing acetonitrile under reflux until the solid dissolved completely, and then cooled to ambient temperature to isolate a yellow-greenish crystal consisting of BDDNPAC, (S)-BINOL, and water, which was analyzed by single crystal X-ray structural analysis. Enantiopure (S)- and (R)-1,1′-bi-2-naphthols were obtained in high yield after decomposition of the colored crystalline complex and evaporation of the acetonitrile solution removed from the complex crystals and successive crystallization. The chiral quaternary ammonium salt BDDNPAC can be recovered and reused without any decrease in efficiency.

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C16H24ClNO2[α]D20=+48.8 (c 1.184, EtOH)Source of chirality: synthesis from threo-(1S,2S)-2-amino-1-(4′-nitrophenyl)-1,3-propanediolAbsolute configuration: (1S,2S)

C38H39ClNO7[α]D20=-25.9 (c 1.012, DMF)Source of chirality: synthesis from BDDNPAC and racemic BINOLAbsolute configuration: (1S,2S,S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 17, Issue 5, 6 March 2006, Pages 854–859
نویسندگان
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