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Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines

2010; American Chemical Society; Volume: 13; Issue: 3 Linguagem: Inglês

10.1021/ol1027305

1523-7060

Joseph J. Badillo, G.E. Arevalo, James C. Fettinger, Annaliese K. Franz,

Synthesis and Catalytic Reactions

A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.