38649-20-6Relevant articles and documents
Novel highly efficient absolute optical resolution method by serial combination of two asymmetric reactions from acetylene monomers having racemic substituents
Aoki, Toshiki,Kaneko, Takashi,Liu, Lijia,Suzuki, Junpei,Tang, Yanan,Teraguchi, Masahiro
supporting information, p. 450 - 461 (2022/01/15)
For general optical resolution, an optical resolution agent is necessary, and the best agent should be selected for each racemic compound. In this study, we will report that a novel optical resolution method by circularly polarized light (CPL) without any
Zn-Catalyzed tert-Butyl Nicotinate-Directed Amide Cleavage as a Biomimic of Metallo-Exopeptidase Activity
Wybon, Clarence C. D.,Mensch, Carl,Hollanders, Charlie,Gadais, Charlène,Herrebout, Wouter A.,Ballet, Steven,Maes, Bert U. W.
, p. 203 - 218 (2018/01/17)
A two-step catalytic amide-to-ester transformation of primary amides under mild reaction conditions has been developed. A tert-butyl nicotinate (tBu nic) directing group is easily introduced onto primary amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate. A weak base (Cs2CO3 or K2CO3) at 40-50 °C can be used provided that 1,1′-bis(dicyclohexylphosphino)ferrocene is selected as ligand. The tBu nic activated amides subsequently allow Zn(OAc)2-catalyzed nonsolvolytic alcoholysis in tBuOAc at 40-60 °C under neutral reaction conditions. The activation mechanism is biomimetic: the C3-ester substituent of the pyridine in the directing group populates the trans-conformer suitable for Zn-chelation, C=Oamide-Zn-Ndirecting group, and Zn-coordinated alcohol is additionally activated as a nucleophile by hydrogen bonding with the acetate ligand of the catalyst. Additionally, the acetate ligand assists in intramolecular O-to-N proton transfer. The chemoselectivity versus other functional groups and compatibility with challenging reaction partners, such as peptides, sugars, and sterols, illustrates the synthetic applicability of this two-step amide cleavage method. The tBu nic amides do not require purification before cleavage. Preliminary experiments also indicate that other weak nucleophiles can be used such as (hetero)arylamines (transamidation) as exemplified by 8-aminoquinoline.
Dimethylmalonyltrialkylphosphoranes: Probing the steric effect on phosphorus and its stereochemical consequence in esterification reactions of chiral secondary alcohols
Dyck,Zavorine,Robertson,Capretta,Larichev,Britten,McNulty
, p. 2548 - 2552 (2007/10/03)
High chemical yields and high levels of stereochemical inversion are demonstrated in the phosphorane-mediated esterification reaction of chiral alcohols with non-hindered carboxylic acids through the incorporation of sterically non-hindered alkyl groups o