406920-74-9Relevant academic research and scientific papers
Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis
Cruz, Faben A.,Zhu, Yamin,Tercenio, Quentin D.,Shen, Zengming,Dong, Vy M.
supporting information, p. 10641 - 10644 (2017/08/15)
We report an enantioselective coupling between alkynes and indoles. A Rh-hydride catalyst isomerizes alkynes to generate a metal-allyl species that can be trapped with both aromatic and heteroaromatic nucleophiles.
Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation
Holland, Mareike C.,Metternich, Jan Benedikt,Daniliuc, Constantin,Schweizer, W. Bernd,Gilmour, Ryan
supporting information, p. 10031 - 10038 (2015/07/07)
Substituting N-methylpyrrole for N-methyindole in secondary-amine-catalysed Friedel-Crafts reactions leads to a curious erosion of enantioselectivity. In extreme cases, this substrate dependence can lead to an inversion in the sense of enantioinduction. Indeed, these closely similar transformations require two structurally distinct catalysts to obtain comparable selectivities. Herein a focussed molecular editing study is disclosed to illuminate the structural features responsible for this disparity, and thus identify lead catalyst structures to further exploit this selectivity reversal. Key to effective catalyst re-engineering was delineating the non-covalent interactions that manifest themselves in conformation. Herein we disclose preliminary validation that intermolecular aromatic (CH-π and cation-π) interactions between the incipient iminium cation and the indole ring system is key to rationalising selectivity reversal. This is absent in the N-methylpyrrole alkylation, thus forming the basis of two competing enantio-induction pathways. A simple L-valine catalyst has been developed that significantly augments this interaction.
Highly stereoselective imidazolethiones mediated Friedel-Crafts alkylation of indole derivatives
Liang, Xianrui,Li, Shuangmin,Su, Weike
supporting information; experimental part, p. 289 - 291 (2012/01/31)
The asymmetric Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes was promoted by the novel imidazolethiones to afford the corresponding adducts in moderate to excellent yields and high enantioselectivities under mild reaction conditions.
Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine
Akagawa, Kengo,Yamashita, Takuhiro,Sakamoto, Seiji,Kudo, Kazuaki
supporting information; experimental part, p. 5602 - 5604 (2011/02/22)
The asymmetric Friedel-Crafts-type alkylation in aqueous media was realized by the resin-supported N-terminal prolyl peptide catalyst having a polyleucine tether. The hydrophobic polyleucine chain in the peptide catalyst was essential for the reaction eff
