کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5264589 | 1385260 | 2013 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Synthesis of optically active α-(nonafluoro-tert-butoxy)carboxylic acids
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موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
Three novel α-(nonafluoro-tert-butoxy)carboxylic esters were synthesized by two methods: the Mitsunobu reaction of optically active (S)-α-hydroxycarboxylic esters and the Williamson synthesis starting from the corresponding O-mesyl derivatives. Both procedures from ethyl (S)-lactate resulted in the formation of a fluorous optically active (R)-lactic acid ester derivative, while the reactions from methyl (S)-mandelate took place with racemization. The proposed mechanism of this racemization is described. The conversion of methyl (S)-phenyllactate under Mitsunobu conditions was also stereospecific, but the reaction of its O-mesyl derivative yielded a mixture of substitution and elimination products. The optical purity of the α-(nonafluoro-tert-butoxy)carboxylic acids prepared by the hydrolysis of the above esters was determined by 1H NMR spectroscopy.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 54, Issue 13, 27 March 2013, Pages 1730-1733
Journal: Tetrahedron Letters - Volume 54, Issue 13, 27 March 2013, Pages 1730-1733
نویسندگان
Tamás Csóka, Anikó Nemes, Dénes Szabó,