62506-81-4Relevant articles and documents
Can a Ketone Be More Reactive than an Aldehyde? Catalytic Asymmetric Synthesis of Substituted Tetrahydrofurans
Lee, Sunggi,Bae, Han Yong,List, Benjamin
, p. 12162 - 12166 (2018)
O-heterocycles bearing tetrasubstituted stereogenic centers are prepared via catalytic chemo- and enantioselective nucleophilic additions to ketoaldehydes, in which the ketone reacts preferentially over the aldehyde. Five- and six-membered rings with both aromatic and aliphatic substituents, as well as an alkynyl substituent, are obtained. Moreover, 2,2,5-trisubstituted and 2,2,5,5-tetrasubstituted tetrahydrofurans are synthesized with excellent stereoselectivities. Additionally, the synthetic utility of the described method is demonstrated with a three-step synthesis of the side chain of anhydroharringtonine.
Visible-Light Photocatalytic Preparation of 1,4-Ketoaldehydes and 1,4-Diketones from α-Bromoketones and Alkyl Enol Ethers
García-Santos, William H.,Mateus-Ruiz, Jeferson B.,Cordero-Vargas, Alejandro
supporting information, p. 4092 - 4096 (2019/06/17)
A Ru2+-photocatalyzed, visible-light-mediated ATRA reaction for the straightforward preparation of 1,4-ketoaldehydes, 1,4-diketones, and 1,4-ketoesters, which are of difficult access by other means, is reported herein. This method employs readily accessible α-bromoketones and alkyl vinyl ethers as starting materials, allowing the construction of secondary, tertiary, and challenging quaternary centers. In addition, the synthetic usefulness of this method is illustrated by applying it to the construction of substituted pyrroles.
Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes
Mondal, Keshab,Mondal, Buddhadeb,Pan, Subhas Chandra
, p. 4835 - 4840 (2016/07/06)
An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi