手性叔胺催化 3-芳基香豆素与 2,3-丁二烯酸酯的不对称 [4 + 2] 环化反应。

Chiral Tertiary Amine Catalyzed Asymmetric [4 + 2] Cyclization of 3-Aroylcoumarines with 2,3-Butadienoate.

机构信息

Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China.

Jiangxi Provincial Research of Targeting Pharmaceutical Engineering Technology, Shangrao Normal University, Shangrao 334001, China.

出版信息

Molecules. 2021 Jan 18;26(2):489. doi: 10.3390/molecules26020489.

DOI:10.3390/molecules26020489

PMID:33477686

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7831925/

Abstract

Coumarins and 2-pyran derivatives are among the most commonly found structural units in natural products. Therefore, the introduction of 2-pyran moiety into the coumarin structural unit, i.e., dihydrocoumarin-fused dihydropyranones, is a potentially successful route for the identification of novel bioactive structures, and the synthesis of these structures has attracted continuing research interest. Herein, a chiral tertiary amine catalyzed [4 + 2] cyclization of 3-aroylcoumarines with benzyl 2,3-butadienoate was reported. In the presence of Kumar's 6'-(4-biphenyl)-β-iso-cinchonine, the desired dihydrocoumarin-fused dihydropyranone products could be obtained in up to 97% yield and 90% ee values.

摘要

香豆素和 2-吡喃衍生物是天然产物中最常见的结构单元之一。因此，在香豆素结构单元中引入 2-吡喃部分，即二氢香豆素-稠合二氢吡喃酮，是鉴定新型生物活性结构的潜在成功途径，这些结构的合成一直引起人们的研究兴趣。在此，报道了手性叔胺催化的 3-芳基香豆素与苄基 2,3-丁二烯酸酯的[4+2]环化反应。在库马尔 6'-(4-联苯基)-β-异奎宁的存在下，以高达 97%的收率和 90%的对映选择性得到了所需的二氢香豆素-稠合二氢吡喃酮产物。