Issue 65, 2018

Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

Abstract

By means of the direct condensation of N-aminoethylpyrroles and isatins, followed by a chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction, a new class of valuable chiral 3′,4′-dihydro-2′H-spiro[indoline-3,1′-pyrrolo[1,2-a]pyrazin]-2-ones bearing a quaternary carbon stereocenter were successfully synthesized in good to excellent yields and with moderate to good enantioselectivities under mild reaction conditions.

Graphical abstract: Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

Supplementary files

Article information

Article type
Paper
Submitted
09 Aug 2018
Accepted
17 Oct 2018
First published
01 Nov 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 37035-37039

Synthesis of six-membered spirooxindoles via a chiral Brønsted acid-catalyzed asymmetric intramolecular Friedel–Crafts reaction

H. Chen, Y. Zhang, Y. Zhang, X. He, Z. Zhang, H. Liang, W. He, X. Jiang, X. Chen and L. Qiu, RSC Adv., 2018, 8, 37035 DOI: 10.1039/C8RA06710D

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