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

Abstract

Samarium diiodide (SmI₂)-mediated desymmetrization of a meso-cyclic 1,3-dione pinacol coupling is described. 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.