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Straightforward stereoselective synthesis of spiro-epoxyoxindoles.

Organic letters (2007-03-31)
Verena Schulz, Marion Davoust, Margareth Lemarié, Jean-François Lohier, Jana Sopkova de Oliveira Santos, Patrick Metzner, Jean-François Brière
ABSTRACT

[reaction: see text] The in situ preparation of a sulfonium ylide reagent achieved the highly diastereoselective epoxidation of isatins, so that a new and straightforward access to biologically significant spiro-epoxyoxindoles is provided. The first investigations of an asymmetric version are reported with enantiopure sulfides.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Methylisatin, 97%