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活性氮杂芳烃的直接环丙烷化反应——位点和立体选择性的去芳构化反应

Direct cyclopropanation of activated N-heteroarenes site- and stereoselective dearomative reactions.

作者信息

Lee Jiyoun, Ko Donguk, Park Hyunju, Yoo Eun Jeong

机构信息

Department of Applied Chemistry , Kyung Hee University , Yongin , 17104 , Republic of Korea . Email:

出版信息

Chem Sci. 2020 Jan 10;11(6):1672-1676. doi: 10.1039/c9sc06369b. eCollection 2020 Feb 14.

Abstract

A divergent cyclopropanation reaction has been accomplished the dearomative addition of sulfur ylides to activated N-heteroarenes. A series of biologically significant molecular skeletons was obtained by the direct cyclopropanation of quinolinium zwitterions. Furthermore, a straightforward synthetic route to optically enriched cyclopropane-fused heterocycles was developed using sulfur ylides as chiral nucleophiles in the 1,4-dearomative reaction.

摘要

通过硫叶立德对活化的氮杂芳烃进行去芳构化加成,实现了一种发散性环丙烷化反应。通过喹啉鎓两性离子的直接环丙烷化反应,得到了一系列具有生物学意义的分子骨架。此外,在1,4-去芳构化反应中,使用硫叶立德作为手性亲核试剂,开发了一条直接合成光学富集的环丙烷稠合杂环的路线。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/66bb/7069384/273a3669f8c7/c9sc06369b-s1.jpg

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