Issue 25, 2021

Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles

Abstract

The efficient catalytic activation of donor–acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46–95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks containing four stereogenic centers including all-carbon quaternary centers were obtained.

Graphical abstract: Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles

Supplementary files

Article information

Article type
Edge Article
Submitted
25 fev 2021
Accepted
04 may 2021
First published
05 may 2021
This article is Open Access

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

Chem. Sci., 2021,12, 8706-8712

Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles

V. Pirenne, E. G. L. Robert and J. Waser, Chem. Sci., 2021, 12, 8706 DOI: 10.1039/D1SC01127H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements