Issue 6, 2020

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

Abstract

A divergent cyclopropanation reaction has been accomplished via 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.

Graphical abstract: Direct cyclopropanation of activated N-heteroarenes via site- and stereoselective dearomative reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Dec 2019
Accepted
30 Dec 2019
First published
10 Jan 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 1672-1676

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

J. Lee, D. Ko, H. Park and E. J. Yoo, Chem. Sci., 2020, 11, 1672 DOI: 10.1039/C9SC06369B

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