Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.



Lanthanide amide-catalyzed one-pot functionalization of isatins: synthesis of spiro[cyclopropan-1,3′-oxindoles] and 2-oxoindolin-3-yl phosphates

Author affiliations

Abstract

Lanthanide amide-catalyzed one-pot reaction of isatins, dialkyl phosphite, and activated alkenes was developed and a series of spiro[cyclopropan-1,3′-oxindoles] were obtained in moderate to excellent yields. The reaction is stereoselective and the two substituents at the 2 and 3-positions of the cyclopropane in the major product are in the trans configuration. A four-step mechanism involving the Pudovik reaction, Brook rearrangement, Michael addition, and intramolecular nucleophilic substitution is proposed, and an umpolung strategy was used in the process.

Graphical abstract: Lanthanide amide-catalyzed one-pot functionalization of isatins: synthesis of spiro[cyclopropan-1,3′-oxindoles] and 2-oxoindolin-3-yl phosphates

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 15 Mar 2017, accepted on 18 Apr 2017 and first published on 18 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00640C
Citation: Org. Biomol. Chem., 2017, Advance Article
  •   Request permissions

    Lanthanide amide-catalyzed one-pot functionalization of isatins: synthesis of spiro[cyclopropan-1,3′-oxindoles] and 2-oxoindolin-3-yl phosphates

    C. Peng, J. Zhai, M. Xue and F. Xu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00640C

Search articles by author