51224-07-8Relevant academic research and scientific papers
Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes
Chen, Xingpeng,Lin, Chao,Du, Hongguang,Xu, Jiaxi
, p. 1647 - 1661 (2019)
An efficient method for the direct synthesis of aziridine-containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C?N bonds of aziridines through an iminium-mediated self-ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The (S)-2-alkylaziridine-derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate-catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes. (Figure presented.).
An improved and mild wenker synthesis of aziridines
Li, Xinyao,Chen, Ning,Xu, Jiaxi
experimental part, p. 3423 - 3428 (2010/11/21)
The conventional Wenker synthesis of aziridines from vicinal amino alcohols has been modified by employing mild reaction conditions. Amino alcohols were converted into their hydrogen sulfates with chlorosulfonic acid. The sulfates were cyclized with sodium hydroxide, and even with non-nucleophilic sodium carbonate. The current, improved method extends the scope of the typical Wenker synthesis and is applicable to unstable amino alcohols in hot sulfuric acid and to unstable sulfates which favor elimination and hydroxide displacement in the presence of strong base. Georg Thieme Verlag Stuttgart.
A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines
Chen, Ning,Jia, Weiyi,Xu, Jiaxi
experimental part, p. 5841 - 5846 (2010/03/03)
Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid, oxidation of the thiazolidine-2-thione intermediates generated from, vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines.
Expeditious and practical synthesis of various substituted taurines from amino alcohols
Zhang, Wei,Wang, Boyuan,Chen, Ning,Du, Da-Ming,Xu, Jiaxi
, p. 197 - 200 (2008/12/20)
Various substituted taurines have been synthesized expeditiously and practically in satisfactory to good yields directly from amino alcohols using a two-step, one-pot procedure, in which the amino alcohols undergo sulfuric acid esterification and subsequent sodium sulfite substitution. Treatment of amino-substituted secondary alcohols using the same procedure gave 2-substituted or 1,2-disubstituted taurines, indicating the formation of aziridines as intermediates during the substitution step. This method is one of the most efficient routes for preparing structurally diverse 2-substituted and 1,2- and 2,2-disubstituted taurines. Georg Thieme Verlag Stuttgart.
Compounds with Bridgehead Nitrogen. Part 43. The Reaction between trans-2-Aminocycloalkanethiols and Formaldehyde
Barkworth, Peter M. R.,Crabb, Trevor A.
, p. 2777 - 2782 (2007/10/02)
trans-2-Aminocyclopentanethiol condenses with formaldehyde to give rel-(3aR,6aR,9aR,12aR)-6,12-methanoperhydrodicyclopentanodithiadiazecine, whereas trans-2-aminocyclohexanethiol and trans-2-aminocycloheptanethiol give 1:1 mixture of diastereomeric bis(perhydrocycloalkanothiazol-3-yl)methanes.
