“On water” direct catalytic vinylogous Henry (nitroaldol) reactions of isatins for the efficient synthesis of isoxazole substituted 3-hydroxyindolin-2-ones

The first example of an "on water" direct catalytic vinylogous Henry addition of 3,5-dialkyl-4-nitroisoxazoles to isatins is described, giving products in excellent yields and up to excellent diastereoselectivities. A remarkable rate-enhancement by water was observed under mild conditions....

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2015-01, Vol.17 (6), p.3266-3270
Main Authors: Zhang, Yong, Wei, Biao-Wen, Lin, Hui, Zhang, Ling, Liu, Jin-Xiang, Luo, Hai-Qing, Fan, Xiao-Lin
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Derivatives
Synthesis (chemistry)
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The first example of an "on water" direct catalytic vinylogous Henry addition of 3,5-dialkyl-4-nitroisoxazoles to isatins is described, giving products in excellent yields and up to excellent diastereoselectivities. A remarkable rate-enhancement by water was observed under mild conditions. This approach provides a highly efficient and environmentally benign access to medicinally important isoxazole substituted 3-hydroxy-2-oxindole derivatives.
ISSN:1463-9262
1463-9270
DOI:10.1039/c5gc00503e