1125-90-2Relevant articles and documents
Photosensitized Electron-Transfer Reaction of 3-Aryl-2-methyloxaziridine: Direct Deoxygenation from the Isomeric Arylnitrone
Iwano, Yasunori,Kawamura, Yasuhiko,Miyoshi, Hiroki,Yoshinari, Toshifumi,Horie, Tokunaru
, p. 2348 - 2350 (1994)
Photosensitized electron-transfer reactions of 3-aryl-2-methyloxaziridines gave mainly the corresponding benzaldehydes, whereas the isomeric nitrones gave imines as well as aldehydes.Deoxygenation of the nitrone occurred via the nitrone cation radical under the reaction conditions.An aryl substituent effect on the reaction and isomerizations of both cation radicals are also discussed.
Synthesis of N-methyl imines in the presence of poly(N-vinylpyridine) as a reusable solid base catalyst by a mechanochemical process
Khaligh, Nader Ghaffari,Abbo, Hanna S.,Titinchi, Salam J. J.
, p. 901 - 910 (2017)
The synthesis of N-methyl imines was performed in the presence of catalytic amounts of poly(4-vinylpyridine) in high yields and rapidly at room temperature by a ball milling process. This new method has some advantages including good yields for relatively unreactive carbonyl compounds and short reaction times as well as being green in terms of avoiding the use of toxic reagents and solvents. The major advantage of this process is that the catalyst can be easily regenerated and reused several times without any significant loss of activity.
Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron
Chen, Dongping,Li, Kaidi,Tang, Wenjun,Xu, Guangqing,Xu, Ronghua,Zhou, Mingkang
supporting information, p. 10337 - 10342 (2020/07/04)
We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.
Epoxide-Mediated Stevens Rearrangements of α-Amino-Acid-Derived Tertiary Allylic, Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin-2-ones
Jin, You-Xiang,Yu, Bang-Kui,Qin, Si-Ping,Tian, Shi-Kai
supporting information, p. 5169 - 5172 (2019/03/28)
A new strategy has been established for the synthesis of polysubstituted morpholin-2-ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α-amino acid-derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl-, allenyl-, and benzyl-substituted morpholin-2-ones, respectively, in moderate-to-good yields with high regioselectivity. The process involves [2,3]- and [1,2]-Stevens rearrangements of quaternary ammonium ylide intermediates and constitutes a very convenient method to prepare polysubstituted morpholin-2-ones through tandem formation of C?N, C?O, and C?C bonds. Moreover, replacing epoxides with aziridines permitted the synthesis of polysubstituted piperazin-2-ones.
