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Stereoselective synthesis of spirooxindoles by palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins.

Organic letters (2009-07-30)
Ryo Shintani, Shin-ya Hayashi, Masataka Murakami, Momotaro Takeda, Tamio Hayashi
ABSTRACT

A new synthetic method of spirooxindole derivatives has been developed by way of a palladium-catalyzed decarboxylative cyclization of gamma-methylidene-delta-valerolactones with isatins. By employing a newly prepared phosphoramidite ligand, the reaction proceeds smoothly with excellent diastereoselectivity. Preliminary results of its application to asymmetric catalysis using a chiral phosphoramidite ligand are also described.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
δ-Valerolactone, technical grade