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

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 carb...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2018-11, Vol.8 (65), p.3735-3739
Main Authors: Chen, Hui-Xuan, Zhang, Yaqi, Zhang, Yuyang, He, Xuefeng, Zhang, Zhen-Wei, Liang, Hao, He, Wenhuan, Jiang, Xiaoding, Chen, Xiangmeng, Qiu, Liqin
Format: Article
Language:
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. A chiral phosphoric acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction for the synthesis of 3′,4′-dihydro-2′ H -spiro[indoline-3,1′-pyrrolo[1,2- a ]pyrazin]-2-ones.
ISSN:2046-2069
DOI:10.1039/c8ra06710d