کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5273888 1385500 2008 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enantioselective arylation of aldehydes catalyzed by a soluble optically active polybinaphthols ligand
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Enantioselective arylation of aldehydes catalyzed by a soluble optically active polybinaphthols ligand
چکیده انگلیسی

A soluble chiral polymer ligand was synthesized by the polymerization of (R)-6,6′-dibutyl-3,3′-diformyl-2,2′-binaphthol (R-M-1) with 2,5-diaminopyridine (M-2) via a nucleophilic addition-elimination reaction. While arylboronic acids were used as the source of the transferable aryl group, the chiral polybinaphthols ligand in combination with Et2Zn without Ti(OiPr)4 exhibited higher enantioselectivity in asymmetric addition to aromatic aldehydes than alphatic aldehydes. When aromatic aldehydes with electron-withdrawing groups were chosen as substrates, the resulting diarylmethanols were produced in higher ee values than those with electron-donating groups as substrates. 2-Naphthaldehyde used as a substrate afforded product in 95% ee, which could be ascribed to the steric effect influence on this asymmetric arylation reaction. Moreover, the chiral polymer was easily recovered and reused, but exhibited a decrease of enantioselectivity in the third recycle.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 49, Issue 48, 24 November 2008, Pages 6823-6826
نویسندگان
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