79102-27-5Relevant articles and documents
Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: Novel stereoselective pathways to aziridines or oxazolines
Nishimura, Masaaki,Minakata, Satoshi,Takahashi, Toru,Oderaotoshi, Yoji,Komatsu, Mitsuo
, p. 2101 - 2110 (2007/10/03)
Chiral nitridomanganese complex 1 was found to be a highly potential N1 unit source for the asymmetric synthesis of aziridines and 2-oxazolines from olefins such as styrene and its derivatives. When sulfonyl chlorides were employed as activators of the complex in the presence of pyridine, pyridine N-oxide, and a silver salt, the reaction of olefins with complex 1 proceeded smoothly to afford the N-sulfonylated aziridines. The aziridination of styrene derivatives with complex 1 using 2-trimethylsilylethanesulfonyl chloride (SESC1) gave the N-SES-aziridines, which were easily converted into chiral N-unsubstituted aziridines. It was found that the reaction was applicable to the asymmetric synthesis of 2-oxazolines from olefins when acyl chlorides were employed as activators. Complex I provided an effective asymmetric environment for trans-disubstituted styrenes in the reaction (up to 92% ee). This is the first example of a direct asymmetric synthesis of 2-oxazolines from olefins. Additional experiments, conducted during the course of this investigation, suggest that the isomerization of the N-acylaziridine intermediate is involved in this reaction.
Ring Opening of Aziridines by Different Fluorinating Reagents: Three Synthetic Routes to α,β-Fluoro Amines with Different Stereochemical Pathways
Alvernhe, Gerald M.,Ennakoua, Christine M.,Lacombe, Sylvie M.,Laurent, Andre J.
, p. 4938 - 4948 (2007/10/02)
The syntheses of α,β-fluoro amines from the reaction of secondary aziridines with either Olah's reagent (HF, pyridine) or anhydrous hydrogen fluoride and of N-activated aziridines with partially neutralized Olah's reagent (NR3-nHF) are reported.The stereo
