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. 2013 Jan 14;11(2):244-7.
doi: 10.1039/c2ob27008k. Epub 2012 Nov 19.

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

Sandeep Rana  1 , Amarnath Natarajan
Affiliations

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

Sandeep Rana et al. Org Biomol Chem. .

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.

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Figures

Fig. 1
Fig. 1
Biologically relevant α-methylene-γ-butyrolactones and oxindole motifs.
Fig. 2
Fig. 2
Overlay of 1H-NMR and 1D-NOE difference NMR spectra.
Scheme 1
Scheme 1
Indium metal mediated Barbier-type reaction between isatin and methyl 2-(bromomethyl)acrylate.
Scheme 2
Scheme 2
Overall routes to study different configurations.
See this image and copyright information in PMC

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