- Iron-catalyzed aziridination reactions
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A small quantity of iron(II) triflate (2.5 to 5 mol%) catalyzes the aziridination reactions of enol silyl ethers with tosylimino(iodo)benzene (PhINTs) in acetonitrile to give α-N-tosylamido ketones by subsequent aziridine ring opening. Olefins are convert
- Nakanishi, Masafumi,Salit, Anne-Frederique,Bolm, Carsten
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scheme or table
p. 1835 - 1840
(2009/07/09)
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- Novel aziridination of olefins: Direct synthesis from sulfonamides using t-BuOI
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tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for synthesis of aziridines from olefins and sulfonamides. The aziridination of olefins was achieved by using sulfonamides with t-BuOI. Our preliminary findings represent the example of met
- Minakata, Satoshi,Morino, Yoshinobu,Oderaotoshi, Yoji,Komatsu, Mitsuo
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p. 3337 - 3339
(2008/09/19)
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- Asymmetric N1 unit transfer to olefins with a chiral nitridomanganese complex: Novel stereoselective pathways to aziridines or oxazolines
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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.
- Nishimura, Masaaki,Minakata, Satoshi,Takahashi, Toru,Oderaotoshi, Yoji,Komatsu, Mitsuo
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p. 2101 - 2110
(2007/10/03)
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- A novel procedure for the synthesis of aziridines: Application of Simmons-Smith reagents to aziridination
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The reaction of Simmons-Smith carbenoids with imines in the presence of sulfides provides N-(p-toluenesulfonyl)- and N-[(1,1,1-trimethylsilyl)ethyl]sulfonyl-substituted aziridines in high yield.
- Aggarwal, Varinder K,Stenson, Rachel A.,Jones, Ray V.H.,Fieldhouse, Robin,Blacker, John
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p. 1587 - 1589
(2007/10/03)
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