1025403-22-8Relevant academic research and scientific papers
A novel organocatalytic asymmetric transfer hydrogenation of α,β-unsaturated aldehydes
Zhang, Bao-Hua,Shi, Lan-Xiang,Guo, Rui-Xia
, p. 2152 - 2154 (2013)
α,β-Unsaturated aldehydes reacted with diimide (diazene) in the presence of optically active ammonium salt 1 as a catalyst to give the corresponding saturated aldehydes in excellent yields and up to 98: 2 er. Attractive features of the asymmetric transfer hydrogenation are its high yields, and chemo-, and enantioselectivities.
CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes
Zhou, Yujing,Bandar, Jeffrey S.,Liu, Richard Y.,Buchwald, Stephen L.
supporting information, p. 606 - 609 (2018/01/26)
The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.
Palladium/chiral amine co-catalyzed enantioselective β-arylation of α,β-unsaturated aldehydes
Ibrahem, Ismail,Ma, Guangning,Afewerki, Samson,C?rdova, Armando
supporting information, p. 878 - 882 (2013/02/23)
Palladium and a simple chiral amine are used as co-catalysts for the enantioselective conjugate addition of aryl boronic acids to α,β-unsaturated aldehydes (see scheme). The synthetic utility of this co-catalyzed reaction was demonstrated in the short tot
Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: Application to the synthesis of β-aryl-γ-lactones and β-aryl aldehydes
Oliveira, Caio C.,Angnes, Ricardo A.,Correia, Carlos Roque D.
, p. 4373 - 4385 (2013/06/27)
We describe herein a synthetically useful method for the enantioselective intermolecular Heck-Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of β-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of β-aryl-γ-lactones and β-aryl aldehydes, which play a vital role as key intermediates in the synthesis of the biologically active compounds, such as (R)-baclofen, (R)-rolipram, (S)-curcumene, (S)-dehydrocurcumene, and (S)-tumerone.
Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether
Akagawa, Kengo,Akabane, Hajime,Sakamoto, Seiji,Kudo, Kazuaki
scheme or table, p. 461 - 466 (2009/09/06)
A resin-supported N-terminal prolyl peptide having a β-turn motif and a polyleucine tether has been developed for the organocatalytic asymmetric transfer hydrogenation under aqueous conditions. Polyleucine accelerated the reaction in a highly enantioselective manner by providing a hydrophobic microenvironment around the prolyl residue. The investigation of catalyst structures indicates that the l-form of polyleucine is essential for both reaction efficiency and enantioselectivity.
Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether
Akagawa, Kengo,Akabane, Hajime,Sakamoto, Seiji,Kudo, Kazuaki
supporting information; experimental part, p. 2035 - 2037 (2009/04/18)
A resin-supported N-terminal prolyl peptide having a β-turn motif and hydrophobic polyleucine chain effectively catalyzed the asymmetric transfer hydrogenation under aqueous conditions. The polyleucine tether provides a hydrophobic cavity in aqueous media that brought about a remarkable acceleration of the reaction. In addition, the polyleucine chain also turned out to be essential for high enantioselectivity.
