Issue 18, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2017
Accepted
18 Apr 2017
First published
18 Apr 2017

Org. Biomol. Chem., 2017,15, 3968-3974

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, 15, 3968 DOI: 10.1039/C7OB00640C

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