Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.

ABSTRACT: 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.

SUBMITTER: Badillo JJ 

PROVIDER: S-EPMC4275133 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature