کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5217583 1383300 2013 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Mechanistic study of asymmetric Michael addition of malonates to enones catalyzed by a primary amino acid lithium salt
چکیده انگلیسی

A mechanistic study was carried out for the asymmetric Michael addition reaction of malonates to enones catalyzed by a primary amino acid lithium salt to elucidate the origin of the asymmetric induction. A primary β-amino acid salt catalyst, O-TBDPS β-homoserine lithium salt, exhibited much higher enantioselectivity than that achieved with the corresponding catalysts derived from α- and γ-amino acids for this reaction. Detailed studies of the transition states with DFT calculations revealed that the lithium cation and carboxylate group of the β-amino acid salt catalyst have important roles in achieving high enantioselectivity in the Michael addition reaction of malonates to enones.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 69, Issue 47, 25 November 2013, Pages 10003-10008
نویسندگان
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