Jump to main content
Jump to site search


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

Abstract

The lanthanide amide-catalyzed one-pot reaction of isatins, dialkyl phosphite, and activated alkenes was developed and a series of spiro[cyclopropan-1,3′-oxindoles] was 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.

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, Accepted Manuscript
  •   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, Accepted Manuscript , DOI: 10.1039/C7OB00640C

Search articles by author