Enantioselective Synthesis of 6/5-Spirosilafluorenes by Asymmetric Ring Expansion of 4/5-Spirosilafluorenes with Alkynes
Hua Chen, Haixia Zhang, Huimin Du, Yuzhong Kuang, Qinjiao Pang, Lu Gao, Wanshu Wang, Cheng Yang, Zhenlei Song
Abstract
A rhodium-catalyzed asymmetric ring expansion of 4/5-spirosilafluorenes with terminal alkynes has been developed using sterically demanding binaphthyl phosphoramidite ligand. The reaction is not only strategically distinct from cyclization or cycloaddition but also showcases the first enantioselective synthesis of axially chiral 6/5-spirosilafluorenes.
Topics & Concepts
Enantioselective synthesisChemistryPhosphoramiditeCycloadditionSteric effectsRing (chemistry)RhodiumStereochemistryCatalysisLigand (biochemistry)Combinatorial chemistryOrganic chemistryReceptorOligonucleotideDNABiochemistryAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods