کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1313498 1499311 2016 11 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
One-pot synthesis and theoretical calculation for trifluoromethylated pyrrolizidines by 1,3-dipolar cycloaddition with azomethine ylides and β-trifluoromethyl acrylamides
چکیده انگلیسی


• A new one-pot synthesis of trifluoromethylated pyrrolizidines was developed.
• High diastereoselectivity (d.r. ≥ 20/1) was observed in most of cases.
• The chemoselectivity is overcome by the separate addition of reagents.
• The origin of regio- and stereoselectivity were investigated by DFT calculation.

The reaction with β-trifluoromethyl acrylamide 3e and azomethine ylides generated from l-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities.

The reaction with β-trifluoromethyl acrylamide 3e and azomethine ylides generated from l-proline and several aldehydes provided the corresponding trifluoromethylated pyrrolizidines with excellent diastereoselectivity (>20/1) in all cases and moderate regioselectivity (up to 1/5.9). A DFT calculation was also examined to reveal the origin of these stereoselectivities.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Fluorine Chemistry - Volume 189, September 2016, Pages 22–32
نویسندگان
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