- Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N -Bz Aziridines to Allylic Amides
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Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination.
- Wood, Devin P.,Guan, Weiyang,Lin, Song
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supporting information
p. 4213 - 4220
(2021/08/10)
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- Desymmetrization of meso-N-acylaziridines with benzenethiols promoted by α,α-Diaryl-L-prolinols
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α,α-Diaryl-L-prolinols were disclosed to promote the desymmetrization of meso-N-acylaziridines with benzenethiols to afford the products in good yields and moderate enantioselectivities (up to 61% ee), which can be greatly improved to >90% ee after a sing
- Lattanzi, Alessandra,Sala, Giorgio Della
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supporting information; experimental part
p. 1845 - 1848
(2009/08/07)
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- Generation of nitrene by the photolysis of N-substituted iminodibenzothiophene
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(Chemical Equation Presented) To evaluate the ability of dibenzothiophene N-substituted sulfilimines as photochemical nitrene sources, their photolyses in the presence of several trapping reagents, such as sulfides, olefins, and phosphorus compounds, were performed. In the reactions, the corresponding imino-transfer compounds, namely sulfilimines, aziridines, and iminophosphoranes, were formed in good yields, indicating dibenzothiophene N-tosyl and N-acylsulfilimines have a potent nature as nitrogen sources.
- Morita, Hiroyuki,Tatami, Atsushi,Maeda, Tetsuo,Byung, Ju Kim,Kawashima, Wataru,Yoshimura, Toshiaki,Abe, Hitoshi,Akasaka, Takeshi
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scheme or table
p. 7159 - 7163
(2009/04/18)
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- A general process for the haloamidation of olefins. Scope and mechanism
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A methodology is described for the addition of a bromine atom and an amide nitrogen in a trans sense to an olefinic double bond. The process, which is illustrated by numerous examples, involves the use of an N-bromoamide and a Lewis acid as a source of Br
- Yeung, Ying-Yeung,Gao, Xuri,Corey
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p. 9644 - 9645
(2007/10/03)
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- The synthesis of N-benzoyl aziridines from β-benzamidoalkyl phenyl selenides
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β-Benzamidoalkyl phenyl selenides can be oxidised, using mCPBA, to the corresponding selenones which can be cyclised to oxazolines or aziridines depending on the reaction conditions. In neutral or weakly basic conditions the oxazoline is the major product
- Ward, Virginia R.,Cooper, Matthew A.,Ward, A. David
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p. 195 - 201
(2007/10/03)
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- Synthesis of N-acylaziridines from β-amido selenides
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The low temperature oxidation of β-amido selenides with MCPBA affords the corresponding β-amido selenones. In situ treatment of the selenones with KOtBu gives N-acylaziridines in good to excellent yield.
- Ward,Cooper,Ward
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p. 944 - 945
(2007/10/03)
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- Asymmetric ring opening reactions of symmetrical N-acylaziridines with thiols catalyzed by chiral dialkyl tartrate-diethylzinc complexes
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The asymmetric ring opening reaction of 1,2-(N-acylimino)cyclohexanes (N- acylaziridines) with some thiols proceeded in the presence of chiral zinc complexes prepared from diethylzinc and dialkyl L-(+)-tartrate to afford trans 2-(N-acylamino)-1-arylthiocyclohexane in up to 93% cc. The enantioselectivity is highly influenced by the molar ratio of the reactants and the nature of chiral dialkyl tartrate. The chemical structure of dialkyl L-(+)-tartrate-zinc complex is discussed on their 1H NMR spectra and molecular weight.
- Hayashi, Masahiko,Ono, Kazuyuki,Hoshimi, Haruhisa,Oguni, Nobuki
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p. 7817 - 7832
(2007/10/03)
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- Asymmetric Catalysis by Vitamin B12: The Isomerization of Achiral Aziridines to Optically Active Allylic Amines
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Achiral N-acylaziridines are isomerized to optically active N-acyl-allylamines in ee's of up to 95percent by catalytic amounts of cob(I)alamin in MeOH.
- Zhang, Zhong da,Scheffold, Rolf
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p. 2602 - 2615
(2007/10/02)
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- Ring Opening of Aziridines by Different Fluorinating Reagents: Three Synthetic Routes to α,β-Fluoro Amines with Different Stereochemical Pathways
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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
- Alvernhe, Gerald M.,Ennakoua, Christine M.,Lacombe, Sylvie M.,Laurent, Andre J.
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p. 4938 - 4948
(2007/10/02)
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