文献类型：期刊文献

英文题名：Decarboxylative, Diastereoselective and exo -Selective 1,3-Dipolar Cycloaddition for Diversity-Oriented Construction of Structural Spiro[Butyrolactone-Pyrrolidine-Chromanone] Hybrids

作者：Guo, Dong-Gui Li, Zheng Han, Xiao-Xue Zhang, Lei Zhang, Min Liu, Xiong-Li

第一作者：郭东贵

通信作者：Liu, XL[1]

机构：[1]Guizhou Inst Technol, Coll Food & Pharmaceut Engn, Guiyang 550025, Peoples R China;[2]Guizhou Univ, Natl & Local Joint Engn Res Ctr Exploitat Homol R, Exploitat Homol Resources Med & Food, Guiyang 550025, Guizhou, Peoples R China

第一机构：贵州理工学院食品药品制造工程学院

通信机构：corresponding author), Guizhou Univ, Natl & Local Joint Engn Res Ctr Exploitat Homol R, Exploitat Homol Resources Med & Food, Guiyang 550025, Guizhou, Peoples R China.

年份：2021

卷号：32

期号：14

起止页码：1447-1452

外文期刊名：SYNLETT

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000685866700012)】；

基金：We are grateful for the financial support from the NSFC (81760625 and 22061006) and Science and Technology Program of Guizhou Province ([2020]4Y205, [2020]1Z074, [2018]5781, and [2017]7295).NaioNnalSu caiFeo nucendCathoofi(nna81760625NationNalSa cuial enceFoundationofChina22061006ScienceandTechnologyPogamofGuizhouPovince(2020]4Y205ScieneandTechnologyPogamofGuizhouPovince2020]1Z074ScienceandTechnologyPorgamofGuizhouProvince2018]5781)ScienceandTechnologyPogamofGuizhouPovince([20177295)

语种：英文

外文关键词：1; 3-dipolar cycloaddition; chromones; spiro compounds; azomethine ylides; pyrrolidines; lactones

摘要：Inspired by the chemistry and biology of butyrolactones, pyrrolidines, and chromanones, we successfully developed a simple domino 1,3-dipolar cycloaddition of homoserine-lactone-derived azomethine ylides for the construction of biologically important spiro[butyrolactone-pyrrolidine-chromanone] hybrids in the presence of Et (3) N as a catalyst under mild conditions. The reaction is based on the application of carboxylic-acid-activated chromones as dienophiles, followed by a decarboxylation process. This reaction displayed good substrate tolerance and gave the desired products in moderate to good yields with high diastereoselectivities (up to 85% yield and >20:1 diastereomeric ratio) via an exo -transition state. This is the first example of an introduction of a chromanone moiety into a spiro[butyrolactone-pyrrolidine] framework, which might be valuable in medicinal chemistry.