859-65-4Relevant articles and documents
Silica gel-promoted synthesis of multisubstituted spiroindolenines from tryptamines and γ-chloro-α,β-unsaturated ketones
Liu, Qiang-Qiang,Zheng, Chao,You, Shu-Li
, (2020/12/02)
Here we report a one-pot synthesis of multisubstituted spiroindolenines from a series of tryptamine derivatives with γ-chloro-α,β-unsaturated ketones. The reaction sequence consists of base-induced condensation and silica gel-promoted intramolecular Michael addition. The target molecules are afforded in up to 90% yield with up to >20:1 diastereoselectivity.
Stereoselective Visible-Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings
Medici, Fabrizio,Resta, Simonetta,Presenti, Piero,Caruso, Lucia,Puglisi, Alessandra,Raimondi, Laura,Rossi, Sergio,Benaglia, Maurizio
, p. 4521 - 4524 (2021/06/12)
Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal-free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light-driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2-trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D-printed mesoreactor, without any change in the diastereoseletctivity of the process.
Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane
Chen, Xue,Jin, Hongwei,Liu, Yunkui,Wang, Zhen,Zhou, Bingwei,Zhou, Jinyong
supporting information, p. 8021 - 8024 (2021/10/04)
Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific
