1512907-53-7Relevant academic research and scientific papers
Use of allylzinc halide as a source of halide: Differential addition of nucleophiles to Ts-aziridines and aldehydes under similar reaction conditions
Chatterjee, Rana,Samanta, Satyajit,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
, p. 276 - 283 (2019)
We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compou
A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr2
Rajbongshi, Kamal Krishna,Saikia, Indranirekha,Chanu, Loukrakpam Dineshwori,Roy, Subhasish,Phukan, Prodeep
, p. 5423 - 5432 (2016/07/13)
N,N-Dibromo-p-toluene sulfonamide (TsNBr2) has been found to be an effective reagent for various aminofunctionalization reactions. This reagent behaves both as an electrophilic bromine source as well as amine to react with olefins under different conditions to yield aminoether, imidazoline, diamine and amino bromine. The reaction proceeds rapidly under mild conditions with high regioselectivity. Olefins react with TsNBr2 in moist THF to form δ-amino ether at room temperature. Treatment of TsNBr2 with olefin in MeCN at room temperature produced imidazoline in high yield. Further modification of the reaction condition resulted in the development of a one-step procedure for the synthesis of N-acetyl,N′-tosyl diamine derivatives directly from olefin. When the olefin was treated with 2.4 mol equiv of TsNBr2 in the presence of K2CO3, N,N′-ditosyl diamine derivative was obtained in moderate yield. Instantaneous formation of aminobromine was observed when an olefin was treated with the reagent in dry CH2Cl2 at room temperature.
Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst
Sun, Hongnan,Yang, Chao,Lin, Run,Xia, Wujiong
, p. 2775 - 2780 (2016/02/18)
A mild and efficient procedure was developed for the regioselective ring-opening nucleophilic addition reactions of aziridines via visible light photoredox catalysis, that provides a practical synthetic access to 1,2-bifunctional compounds. Furthermore, the regioselective synthesis of non-racemic amino ethers from chiral aziridine could also be achieved under mild conditions. Finally, a possible reaction mechanism was proposed and further supported by control experiments.
