Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines

Carroccia, Laura; Fioravanti, Stefania; Pellacani, Lucio; Sadun, Claudia; Tardella, Paolo A.

doi:10.1016/j.tet.2011.05.097

Cited by 29 publications

(11 citation statements)

References 30 publications

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“…On the contrary, performing the reaction with ZrCl 4 , while the nitromethane was quantitatively recovered, the 1 H-NMR spectrum of the crude mixture showed only the disappearance of the imine signals, whose hydrolysis is mainly promoted by the presence of Lewis acid. Only working without added catalyst, the expected product 5a was obtained after 1 h of stirring at room temperature by a self-catalyzed addition in which aldimine 3a acts as both base and electrophile [22,23] (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Aza-Henry Reactions on C-Alkyl Substituted Aldimines

et al. 2016

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Abstract:The reactivity of C-CH 3 substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF 3 aldimines, they gave the aza-Henry addition only when ZrCl 4 was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity.

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Section: Resultsmentioning

confidence: 99%

Aza-Henry Reactions on C-Alkyl Substituted Aldimines

et al. 2016

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“…The expected products were obtained in good yields, working at room temperature under solvent‐free conditions and without added catalyst. The aldimine acts as both base and electrophile, and therefore is a good example of green chemistry: the addition proceeds with total atom economy (Scheme ) and with moderate environmental impact, no reaction workup being needed.…”

Section: Resultsmentioning

confidence: 99%

In Pursuit of β‐Amino‐α‐nitro‐β‐(trifluoromethyl) Ketones: Nitro‐Mannich versus Mannich‐Type Reactions

2017

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The reactivity of α‐nitro ketones with trifluoromethyl aldimines has been studied for the first time. Whereas under nitro‐Mannich conditions only the facial stereoselectivity can be controlled, organocatalysed Mannich‐type reactions allowed complete control of the absolute and relative stereoselectivity, leading to highly functionalised β‐amino‐α‐nitro‐β‐(trifluoromethyl) compounds as diastereomerically pure compounds. The structures of the reactants play a key role in the geometrical and/or facial stereoselectivity.

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“…In general, oxaziridines bearing perfluorinated alkyl residues at the C-atom, are more powerful oxidizing agents in comparison with the nonfluorinated analogous [5,11].…”

Section: Resultsmentioning

confidence: 99%

“…However, fluorinated oxaziridines are less well known, and the reported examples mainly originate from perfluorinated starting materials [4]. Recently, oxaziridines derived from fluoral N-alkyl imines were reported [5]. Starting with enantiopure substrates, the corresponding products were obtained in a highly diastereoselective manner.…”

Section: Introductionmentioning

confidence: 99%

A new approach to α-(trifluoromethyl)benzyl substituted oxaziridines

Obijalska

Mlostoń

Utecht

et al. 2013

Journal of Fluorine Chemistry

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The synthesis of N-substituted oxaziridines bearing an alpha-(trifluoromethyl)benzyl substituent at C(3) was achieved by m-CPBA oxidation of the corresponding 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols and their trimethylsilyl protected derivatives, respectively. In all cases, mixtures of diastereoisomers were formed. The prepared oxaziridine derivatives were shown to be able to oxidize thioanisole to thioanisole S-oxide in the presence of methanesulfonic acid. ABSTRACTThe synthesis of N-substituted oxaziridines bearing an ±-(trifluoromethyl)benzyl substituent at C(3) was achieved by m-CPBA oxidation of the corresponding 3-imino-1,1,1-trifluoro-2-arylpropan-2-ols and their trimethylsilyl protected derivatives, respectively. In all cases, mixtures of diastereoisomers were formed. The prepared oxaziridine derivatives were shown to be able to oxidize thioanisole to thioanisole Soxide in the presence of methanesulfonic acid.

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Synthesis of optically active trifluoromethyl substituted diaziridines and oxaziridines

Cited by 29 publications

References 30 publications

Aza-Henry Reactions on C-Alkyl Substituted Aldimines

Aza-Henry Reactions on C-Alkyl Substituted Aldimines

In Pursuit of β‐Amino‐α‐nitro‐β‐(trifluoromethyl) Ketones: Nitro‐Mannich versus Mannich‐Type Reactions

A new approach to α-(trifluoromethyl)benzyl substituted oxaziridines

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