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Titanium(IV)-catalyzed Stereoselective Synthesis of spirooxindole-1-pyrrolines

Titanium(IV)-catalyzed Stereoselective Synthesis of spirooxindole-1-pyrrolines

Joseph J Badillo, Carlos J A Ribeiro, Marilyn M Olmstead, Annaliese K Franz

Org Lett. 2014 Dec 19;16(24):6270-3.

PMID: 25474118

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10361849	Scandium(III) chloride		10361-84-9	Price

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