A Stereoselective Synthesis of Fused Carbocycles with a cis-1,2-Diol Moiety by Desymmetrization: SmI2-Mediated Pinacol Coupling of meso-Cyclic 1,3-Diones

Samarium diiodide (SmI2)-mediated desymmetrization of a meso-cyclic 1,3-dione pinacol coupling is de-scribed. The reaction proceeds with high stereoselectivity to provide fused carbocyclic compounds with three contiguous stereogenic centers featuring an all-carbon quaternary center and a cis-1,2-diol moiety.

Automated summary

This paper describes the desymmetrization of a meso-cyclic 1,3-dione pinacol coupling using samarium diiodide (SmI2). The reaction exhibits high stereoselectivity, resulting in fused carbocyclic compounds with three contiguous stereogenic centers, including an all-carbon quaternary center and a cis-1,2-diol moiety.