147032-71-1Relevant academic research and scientific papers
γ-Selectivity in the Ceric Ammonium Nitrate Promoted Oxidative Addition of Silyl Dienol Ethers to Silyl Enol Ethers
Paolobelli, Anna Belli,Latini, David,Ruzziconi, Renzo
, p. 721 - 724 (1993)
Trimethylsilyl dienol ethers are easily oxidized by ceric ammonium nitrate to give α-carbonylallyl radicals which are able to add to enolic carbon-carbon double bonds with very high γ regioselectivity, allowing the method to be applied to the synthesis of
Enantioselective Synthesis of Spiro-oxiranes: An Asymmetric Addition/Aldol/Spirocyclization Domino Cascade
Choo, Ken-Loon,Mirabi, Bijan,Demmans, Karl Z.,Lautens, Mark
supporting information, p. 21189 - 21194 (2021/08/23)
Enantioenriched spiro-oxiranes bearing three contiguous stereocenters were synthesized using a rhodium-catalyzed asymmetric addition/aldol/spirocyclization sequence. Starting from a linear substrate, the cascade enabled the formation of a spirocyclic framework in a single step. sp2- and sp-hybridized carbon nucleophiles were found to be competent initiators for this cascade, giving arylated or alkynylated products, respectively. Derivatization studies demonstrated the synthetic versatility of both the epoxide and the alkyne moieties of the products. DFT calculations were used to reconcile spectroscopic discrepancies observed between the solution- and solid-state structures of the products.
