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由1,2 - 二苯基乙二胺催化的丙二酸酯对α,β - 不饱和酮的对映选择性迈克尔加成反应。

Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine.

作者信息

Wang Wei, Ye Ling, Shi Zhichuan, Zhao Zhigang, Li Xuefeng

机构信息

College of Chemistry and Environment Protection Engineering, Southwest Minzu University Chengdu 610041 China

Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University Chengdu 610031 China.

出版信息

RSC Adv. 2018 Dec 12;8(73):41699-41704. doi: 10.1039/c8ra07809b.

Abstract

A general and highly enantioselective Michael addition of malonates to cinnamones and chalcones has been developed. The commercially available 1,2-diphenylethanediamine could be directly utilized as the organocatalyst to furnish the desired adducts in satisfactory yield (61-99%) and moderate to excellent enantiopurity (65 to >99% ee). β-Ketoester was also a competent donor and was employed to construct densely functionalized cyclohexenones a tandem Michael-aldol condensation process.

摘要

已开发出一种将丙二酸酯与肉桂酮和查耳酮进行的通用且高度对映选择性的迈克尔加成反应。市售的1,2-二苯基乙二胺可直接用作有机催化剂,以令人满意的产率(61-99%)和中等至优异的对映体纯度(65至>99% ee)提供所需的加合物。β-酮酯也是一种有效的供体,并用于通过串联迈克尔-羟醛缩合过程构建功能密集的环己烯酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7684/9091971/5717eb124b84/c8ra07809b-s1.jpg

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