Preparation of α-amino ketones, β-amino hydroxylamines using asymmetric aza-Henry reactions of N-p-tolylsulfinylimines with nitroethane

Ruano, José Luis Garcı́a; López-Cantarero, Jesús; Haro, Teresa de; Alemán, José V.; Cid, M. B.

doi:10.1016/j.tet.2006.10.021

Cited by 30 publications

(6 citation statements)

References 39 publications

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“…[23] Theo xidative Nef reactionon selectedd iastereoisomeric mixtures using KMnO 4 allowsthe preparation of enantioenriched b-amidosulfinyl ketones in good yield (73-90%).…”

Section: O Xidative Methodsmentioning

confidence: 99%

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

2015

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This review article reports new procedures and practical application of the nitro to carbonyl conversion that appeared in the literature after our\ud comprehensive report published in 2004. Beside traditional and well explored reactant systems, new procedures including the utilization of molecular oxygen and photoredox catalysis have been introduced for the Nef reaction. Of notable interest is the utilizationof the nitro to carbonyl conversion in tandem and cascade processes aimed at the preparation of hetero and carbocyclic derivatives

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“…[23] Theo xidative Nef reactionon selectedd iastereoisomeric mixtures using KMnO 4 allowsthe preparation of enantioenriched b-amidosulfinyl ketones in good yield (73-90%).…”

Section: O Xidative Methodsmentioning

confidence: 99%

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

2015

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“…Among them, the aza-Henry reaction [1,2,3,4], also called nitro-Mannich reaction, involves the nucleophilic addition of nitro alkanes to aldimines and leads to the synthesis of β-nitro amines, valuable compounds containing two vicinal nitrogenated functionalities with different oxidation states. Also for this, the aza-Henry reaction presents important synthetic applications [5,6,7,8], providing access to a wide variety of other organic compounds by functional transformations of the nitro group into other chemical functionalities, such as amines, carbonyl groups, hydroxylamines, oximes, and nitriles.…”

Section: Introductionmentioning

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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“…We envisioned that enantiomerically pure substituted nitropiperidones could be obtained from the Michael addition of β-nitroamines 1 , followed by sulfoxide removal and cyclization (Scheme ). Despite of the low diastereoselectivity anticipated for the Michael addition on the basis of our previous results, the strong acidity of the α-proton to nitro group also made predictable an easy epimerization of the final nitropiperidone favoring one diastereoisomer.…”

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confidence: 53%

An Efficient Method for the Synthesis of Nitropiperidones

et al. 2008

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A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha,beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A very simple experimental procedure involving mild conditions and only one chromatographic purification are the main features of the process.

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Preparation of α-amino ketones, β-amino hydroxylamines using asymmetric aza-Henry reactions of N-p-tolylsulfinylimines with nitroethane

Cited by 30 publications

References 39 publications

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

The Nitro to Carbonyl Conversion (Nef Reaction): New Perspectives for a Classical Transformation

Aza-Henry Reactions on C-Alkyl Substituted Aldimines

An Efficient Method for the Synthesis of Nitropiperidones

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