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Communication | Special issue | Vol 72, No. 1, 2007, pp.199-205
Published online, 6th March, 2007
DOI: 10.3987/COM-07-S(K)59
Studies on Enol Carbonate Chemistry: Stereoselective Construction of Vicinal Quaternary Benzylic Centers in the Bis-oxindole Series

Candice Menozzi, Peter I. Dalko,* and Janine Cossy

*Laboratory of Organic Chemistry, University Paris 5, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France

Abstract

The Steglich-type intramolecular acyl transfer of bis-oxindole enol carbonate derivatives 9a-c affords selectively the monorearranged products 11a-c. In turn, Pd(0)-mediated allyl transfer of the bis-Alloc derivative 9c allows an efficient double C-allylation leading preferentially to the d/l isomer.