کد مقاله کد نشریه سال انتشار مقاله انگلیسی ترجمه فارسی نسخه تمام متن
64544 48361 2016 7 صفحه PDF سفارش دهید دانلود کنید
عنوان انگلیسی مقاله ISI
Experimental and theoretical investigation of the enantioselective hydrogenation of ethyl pyruvate with a Pt catalyst with new non-cinchona chiral modifiers
ترجمه فارسی عنوان
بررسی تجربی و نظری هیدروژنه کردن enantioselective پیروات اتیل با کاتالیزور پلاتین با اصلاح کایرال غیر درخت گنه گنه جدید
کلمات کلیدی
Enantioselectivity؛ پیروات اتیل؛ اصلاح غیر درخت گنه گنه؛ DFT؛ پلاتین
موضوعات مرتبط
مهندسی و علوم پایه مهندسی شیمی کاتالیزور
چکیده انگلیسی


• Ethyl pyruvate was hydrogenated on a Pt/SiO2 catalyst modified with chiral modifiers.
• An enantiomeric excess (ee%) of 63% was obtained with (S)-(+)-1-aminoindan.
• Density Functional Theory calculations allowed predicting ee% obtained experimentally.
• Low ee% for aminoindanol was explained by the noncovalent interaction approach.

The enantioselective hydrogenation of ethyl pyruvate using a Pt/SiO2 catalyst modified with six different chiral modifiers was studied. The chiral modifiers chosen were: (S)-(+)-1-aminoindan, (R)-(−)-1-aminoindan, (1R,2S)-(+)-cis-1- amino-2-indanol, (1S,2R)-(−)-cis-1-amino-2-indanol, (S)-(+)-1-indanol and (R)-(−)-1-indanol.An excess of the (R) enantiomer of the product of 63% and 45% with (S)-(+)-1-aminoindan and (R)-(−)-1-aminoindan modifiers, respectively was obtained. When using (1S,2R)-(−)-cis-1-amino-2-indanol and (1R,2S)-(+)-cis-1-amino-2-indanol, the enantiomeric excess (ee%) obtained was 30% and 5%, respectively, while with both indanols ee% did not exceed 8%. Molecular modeling of the complex formed between the chiral modifier and ethyl pyruvate performed by DFT calculations allowed predicting the values of ee% obtained experimentally. The low ee% value obtained both aminoindanol chiral modifiers were used, could be explained by the analysis of non-covalent interactions (NCI) method. These calculations demonstrated the presence of an intramolecular hydrogen bond in the structure of these modifiers.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Catalysis A: Chemical - Volume 423, November 2016, Pages 233–239
نویسندگان
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