338461-66-8Relevant articles and documents
Efficient access to chiral β-arylamides via asymmetric 1,4-additions of potassium trifluoro(organo)borates
Pucheault, Mathieu,Michaut, Valérie,Darses, Sylvain,Genet, Jean-Pierre
, p. 4729 - 4732 (2004)
This paper describes an efficient enantioselective conjugate addition of highly stable potassium trifluoro(organo)borates to α,β-unsaturated amides. This reaction, catalyzed by chiral rhodium(I) complexes affords Michael adducts with high yields and enant
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.
Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides
Shintani, Ryo,Kimura, Takahiro,Hayashi, Tamio
, p. 3213 - 3214 (2007/10/03)
Rhodium/chiral diene (S,S)-3b complex has been found to effectively catalyze the 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides, furnishing useful β-chiral Weinreb amides in high enantioselectivity. The Royal Society of Chemistry 2005.
