535946-25-9Relevant academic research and scientific papers
Enantioselective Hydroamidation of Enals by Trapping of a Transient Acyl Species
Yuan, Pengfei,Chen, Jiean,Zhao, Jing,Huang, Yong
supporting information, p. 8503 - 8507 (2018/07/14)
An enantioselective synthesis of β-chiral amides through asymmetric and redox-neutral hydroamidation of enals is reported. In this reaction, a chiral N-heterocyclic carbene (NHC) catalyst reacts with enals to generate the homoenolate intermediate. Upon highly enantioselective β-protonation through proton-shuttle catalysis, the resulting azolium intermediate reacts with imidazole to yield the key β-chiral acyl species. This transient intermediate provides access to diversified β-chiral carbonyl derivatives, such as amides, hydrazides, acids, esters, and thioesters. In particular, β-chiral amides can be prepared in excellent yield and ee (40 chiral amides, up to 95 % yield and 99 % ee). This modular strategy overcomes the challenge of disruption of the highly selective proton-shuttling process by basic amines.
Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Amides
Yasukawa, Tomohiro,Saito, Yuuki,Miyamura, Hiroyuki,Kobayashi, Shū
supporting information, p. 8058 - 8061 (2016/09/13)
Cooperative catalysts consisting of chiral Rh/Ag nanoparticles and Sc(OTf)3have been developed that catalyze asymmetric 1,4-addition reactions of arylboronic acids with α,β-unsaturated amides efficiently. The reaction has been considered one of
Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines
Islam, Sk Manirul,Ghosh, Kajari,Roy, Anupam Singha,Molla, Rostam Ali
, p. 900 - 907 (2015/02/19)
A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.
Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor
Watson, Andrew J.A.,Wakeham, Russell J.,Maxwell, Aoife C.,Williams, Jonathan M.J.
supporting information, p. 3683 - 3690 (2014/05/20)
A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.
Ruthenium-catalyzed oxidation of alcohols into amides
Watson, Andrew J.A.,Maxwell, Aoife C.,Williams, Jonathan M.J.
supporting information; experimental part, p. 2667 - 2670 (2009/10/02)
The synthesis of secondary amides from primary alcohols and amines has been developed using commercially available [Ru(p-cymene)CI2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst.
