71027-83-3Relevant academic research and scientific papers
Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine synthesesviaCsp3-H functionalizations
Kaur, Navdeep,Ziegelmeyer, Elizabeth C.,Farinde, Olutayo N.,Truong, Jonathon T.,Huynh, Michelle M.,Li, Wei
supporting information, p. 10387 - 10390 (2021/10/14)
A catalytic benzylic Csp3-H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3-H bonds that enabled the stereoselective synthesis ofcis- andtrans-oxazolines.
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.
Direct asymmetric synthesis of oxazolines from olefins using a chiral nitridomanganese complex: A novel three-component coupling leading to chiral oxazolines
Minakata, Satoshi,Nishimura, Masaaki,Takahashi, Toru,Oderaotoshi, Yoji,Komatsu, Mitsuo
, p. 9019 - 9022 (2007/10/03)
A new synthetic method for chiral oxazolines has been developed by N1 unit transfer to olefins using a chiral nitridomanganese complex. When trans-disubstituted styrenes were treated with chiral complex 1 in the presence of an acid chloride, oxazolines we
Isoquinoline Synthesis via 2-Oxazolines. Part VII. N-Styrylamides as Intermediates in the Pictet-Gams Reaction
Kopczynski, T.
, p. 73 - 84 (2007/10/02)
Attempts have been described aiming at isolation of N-styrylamides in the course of Pictet-Gams reaction.Generation of the compounds as intermediates of the reaction has been demonstrated on grounds of hydroxyamide cyclization, using deuterated chlorophosphoric acid as a dehydrating agent.Key words: amino alcohols, isoquinoline, oxazoline
