10.1021/ol5028128.s002 Joseph J. Badillo Joseph J. Badillo Carlos J. A. Ribeiro Carlos J. A. Ribeiro Marilyn M. Olmstead Marilyn M. Olmstead Annaliese K. Franz Annaliese K. Franz Titanium(IV)-Catalyzed Stereoselective Synthesis of Spirooxindole-1-pyrrolines American Chemical Society 2015 stereoselective Spirooxindole diastereoselectivity pyrroline alkylidene oxindoles enantioenriched spiro cyclization methodology coumarin derivatives spirooxindole chloride Synthesi reversal mol scandium methoxyoxazole chiral Stereoselective malonate alkylidene synthesis 2015-12-17 06:31:52 Dataset https://acs.figshare.com/articles/dataset/Titanium_IV_Catalyzed_Stereoselective_Synthesis_of_Spirooxindole_1_pyrrolines/2045952 A stereoselective cyclization between alkylidene oxindoles and 5-methoxyoxazoles has been developed using catalytic titanium­(IV) chloride (as low as 5 mol %) to afford spiro­[3,3′-oxindole-1-pyrrolines] in excellent yield (up to 99%) and diastereoselectivity (up to 99:1). Using a chiral scandium­(III)–indapybox/BArF complex affords enantioenriched spirooxindole-1-pyrrolines where a ligand-induced reversal of diastereoselectivity is observed. This methodology is further demonstrated for the synthesis of pyrrolines from malonate alkylidene and coumarin derivatives.