An easily available iron catalyst was developed to accomplish the C H functionalization of indoles with a-aryl-a-diazoesters in high yields under mild conditions. The asymmetric C H functionalization of indoles was also realized by using iron complexes of chiral spiro bisoxazolines with up to 78% ee.

An efficient and powerful organocatalytic cascade reaction was achieved for the synthesis of biologically important chiral spiro[pyrrolidin-3,2'-oxindoles] using very simple and readily available starting materials. Three C-C bonds and four contiguous stereogenic centers including one quaternary stereocenter were established in a single operation with reasonable yields and good stereoselectivity.

An efficient synthesis of spiropyrazolones based on organocatalysis is described. The reaction between pyrazolones, enolizable aldehydes and enals is catalyzed by secondary amine catalysts and affords the final spiro compounds bearing four contiguous chiral centers in good yields and excellent diastereo- and enantioselectivities.

A chiral cooperative catalysis of NHC and Brønsted acid for a formal [4+2] reaction of unprotected isatins and enals was developed for the direct synthesis of unprotected spiro[indoline-3,2'-pyran]-2,6'(3'H)-diones in good to excellent yields (up to 95%) with high enantioselectivities (up to >93% ee).

Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η(1)-allylpalladium l...

The catalytic asymmetric three-component 1,3-dipolar cycloaddition of 3-amino oxindoles with aldehydes and nitroolefins under the catalysis of a chiral phosphoric acid is reported. The reaction provides a facile approach to synthesize a diverse array of spiro[pyrrolidine-2,3'-oxindoles] in high yields with excellent diastereo- and enantioselectivities under mild conditions.

Asymmetric epoxidation of various styrenes using carbocyclic oxazolidinone-containing ketone 3 has been investigated. High enantioselectivity (89-93% enantiomeric excess) has been attained for this challenging class of alkenes. Mechanistic studies show that substituents on the ketone catalyst can have electronic influences on secondary orbital interactions, which affects the competition between...

The structures of natural products from a variety of sources contain spirocycles, two rings that share a common atom. The spiro motif is finding increasing inclusion in drug candidates, and as a structural component in several promising classes of chiral ligands used in asymmetric synthesis. Total syntheses of products containing all-carbon spirocycles feature several common methods of ring clo...