Spiro[azetidine-indolines] are important scaffolds in diverse bioactive compounds. Current efforts to synthesize spiro[azetidine-indolines] are limited to chiral spiro[azetidine-2,3'-indolines]. Asymmetric synthesis of structurally similar chiral spiro[azetidine-3,3'-indolines] remains unexplored. In this work, the first copper(I)catalyzed asymmetric Kinugasa/aryl CÀ C coupling cascade reaction is described. This provides a straightforward access to densely functionalized chiral spiro[azetidine-3,3'-indoline]-2,2'-diones in good yields and with high enantioselectivity.

A synthesis of spiroindolinone-isoindolinone skeletons is presented. The protocol is through a Ugi four-component reaction followed by highly efficient and mild copper-catalyzed intramolecular tandem CÀ N/ CÀ C coupling process. Control experiments demonstrated that the formation of CÀ C bond is a copper catalyzed coupling process rather than base promoted nucleophilic aromatic substitution pathway which proposed in Prof. Van der Eycken's palladium catalyst system previously.

A highly efficient and mild sequential nucleophilic addition/ cyclization/copper catalyzed CÀ N coupling reaction of o-iodophenyl isothiocyanates with propargylamines has been realized, which delivers a variety of benzimidazo [2,1-b]thiazole derivatives in good yields. Moreover, this protocol could be performed at gram scale and applied to the concise synthesis of tilomisole.

Spiro[azetidine-indolines] are important scaffolds in diverse bioactive compounds. Current efforts to synthesize spiro[azetidine-indolines] are limited to chiral spiro[azetidine-2,3'-indolines]. Asymmetric synthesis of structurally similar chiral spiro[azetidine-3,3'-indolines] remains unexplored. In this work, the first copper(I)catalyzed asymmetric Kinugasa/aryl CÀ C coupling cascade reaction is described. This provides a straightforward access to densely functionalized chiral spiro[azetidine-3,3'-indoline]-2,2'-diones in good yields and with high enantioselectivity.

Chiral o-aminobenzylamines are synthons for many chiral ligands and catalysts which have been widely used in asymmetric synthesis. Herein, we report a highly efficient and stereoselective addition of Grignard reagent to o-aminosulfinylimine for a range of o-aminosulfinylimines in good yields with good to excellent diastereoselectivity.