کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5220254 1383382 2011 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Highly enantioselective aldol reactions using a tropos dibenz[c,e]azepine organocatalyst
چکیده انگلیسی

The four-step synthesis of a chiral primary tertiary diamine salt, possessing a tropos dibenz[c,e]azepine ring is described. It is shown that 3.5-5 mol % of this salt is capable of promoting highly enantioselective crossed-aldol reactions between cyclohexanone and a series of aromatic aldehydes. In all cases, the aldol reactions proceed with high diastereoselectivity for the anti-aldol product. The outcome of crossed-aldol reactions involving other cyclic ketones and acyclic ketones are also described. All examples involving cyclic ketones result in selectivity for the anti-aldol products, whereas acyclic ketones were found to favour the syn-aldol products. A discussion on the role of the chiral primary tertiary diamine salt in the catalysis of the aldol reactions is also presented.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 67, Issue 52, 30 December 2011, Pages 10164-10170
نویسندگان
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