42925-43-9Relevant articles and documents
Bi(OTf)3-Catalyzed Alkyl-Intercepted Meyer-Schuster Rearrangement of Propargylic Alcohols for the Synthesis of 1,2,3,5-Tetrasubstituted Pentane-1,5-diones
Wang, Zhihai,Sun, Yuxing,Zhang, Qinglin,Pan, Wanyong,Li, Tiantian,Yin, Yan
, p. 3329 - 3340 (2022/02/25)
An alkyl intercepted Meyer-Schuster rearrangement reaction with α,β-unsaturated ketones as the electrophiles was first investigated, which provided a facile method to construct 2-methylene-pentane-1,5-diones. Then the in situ generated 2-methylene-pentane-1,5-diones underwent a Michael addition to give diverse 2-malononitrile methyl substituted pentane-1,5-diones in a one-pot fashion. This transformation was reliable on a gram scale. The high yield, convenient experimental operation, and 100% atom economy made it a valuable method for the construction of 1,2,3,5-tetrasubstituted pentane-1,5-dione derivatives.
Enantioselective Conjugate Azidation of α,β-Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN3
Humbrías-Martín, Jorge,Pérez-Aguilar, M. Carmen,Mas-Ballesté, Rubén,Dentoni Litta, Antonella,Lattanzi, Alessandra,Della Sala, Giorgio,Fernández-Salas, Jose A.,Alemán, José
, p. 4790 - 4796 (2019/09/16)
An enantioselective organocatalytic conjugate azidation of α,β-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst. (Figure presented.).
Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
supporting information, p. 2003 - 2006 (2018/04/16)
A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p