Issue 2, 2013
From the journal:

Organic & Biomolecular Chemistry

Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones†

Sandeep Ranaa  and  Amarnath Natarajan*ab  

* Corresponding authors

a Eppley Institute for Research in Cancer and Allied Diseases, University of Nebraska Medical Center, Omaha, NE, USA

b Department of Chemistry, University of Nebraska, Lincoln, NE, USA
E-mail: anatarajan@unmc.edu
Fax: +1-402-559-3793
Tel: +1-402-559-8270

Abstract

We report an unusual face selective reduction of the exocyclic double bond in the α-methylene-γ-butyrolactone motif of spiro-oxindole systems. The spiro-oxindoles were assembled by an indium metal mediated Barbier-type reaction followed by an acid catalyzed lactonization.

Graphical abstract: Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones

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Article information

DOI
https://doi.org/10.1039/C2OB27008K
Article type
Communication
Submitted
15 Oct 2012
Accepted
07 Nov 2012
First published
14 Nov 2012

Org. Biomol. Chem., 2013,11, 244-247

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Face selective reduction of the exocyclic double bond in isatin derived spirocyclic lactones

S. Rana and A. Natarajan, Org. Biomol. Chem., 2013, 11, 244 DOI: 10.1039/C2OB27008K

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