Copper(i) catalysed cyclisation of unsaturated N-benzoyloxyamines: an aminohydroxylation via radicals

Noack, Michael; Göttlich, Richard

doi:10.1039/b111656h

Cited by 126 publications

(46 citation statements)

References 12 publications

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“…[49] In this paper, treatment of a range of N-benzoyl hydroxylamines with pendant olefins, with 10 % CuPF 6 in the presence of a Lewis acid furnished the oxyaminated products in moderate yields and varying levels of regioselectivity for pyrrolidines over piperidines (Scheme 27).…”

Section: Copper-mediated Reactionsmentioning

confidence: 98%

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Donohoe

Callens

Flores

et al. 2010

Chemistry A European J

259

115

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1,2-Amino alcohols are high-value, versatile functional groups that are found in scores of biologically active molecules and other interesting synthetic targets such as ligands and auxiliaries. Given their prominent position within organic compounds of import, it is no surprise to note that many routes have been developed to access this motif and there are many different starting points from which a synthetic chemist might embark on a synthesis. However, one particular approach stands out from the others, and this is the direct conversion of an alkene to a vicinal amino alcohol derivative (oxyamination). Research in this field has been particularly active in recent years and many interesting new methodologies have been reported. The purpose of this review is to give the reader a tour of the methods that have emerged in the last few years so one can appreciate the myriad of different metals and reagents that can accomplish the oxyamination of alkenes. There are still many challenges to be overcome and, herein, we also outline the areas that are ripe for further development and which bode well for the future.

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Section: Copper-mediated Reactionsmentioning

confidence: 98%

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Donohoe

Callens

Flores

et al. 2010

Chemistry A European J

259

115

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“…1, 2 Nevertheless, the poor regioselectivity of this reaction 3 and the requirement for a toxic and precious osmium catalyst has inspired significant efforts over the last decade to design alternative oxyamination processes based on palladium, 4 platinum, 5 rhodium, 6 gold, 7 copper, 8 hypervalent iodine, 9 and radical reactions. 10 Several enantioselective osmium-free oxyaminations have been reported in an intramolecular context.…”

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confidence: 99%

Iron Catalyzed Asymmetric Oxyamination of Olefins

2012

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The regioselective and enantioselective oxyamination of alkenes with N-sulfonyl oxaziridines is catalyzed by a novel iron(II) bis(oxazoline) complex. This process affords oxazolidine products that can be easily manipulated to yield highly enantioenriched free amino alcohols. The regioselectivity of this process is complementary to that obtained from the analogous copper(II)-catalyzed reaction. Thus, both regioisomers of enantioenriched 1,2-aminoalcohols can be obtained using oxaziridine-mediated oxyamination reactions, and the overall sense of regiochemistry can be controlled using the appropriate choice of inexpensive first-row transition metal catalyst.

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“…19 Next, we examined the reaction of O-benzoyl-N-butyl-N-(2-methylpent-4-en-1-yl)hydroxylamine with model phosphonate 1h, and we obtained the desired amination product 8 exclusively; we detected no cyclization product such as pyrrolidine 9, which might have formed through a previously reported copper-catalyzed 5-exo radical cyclization. 20 On the basis of these results, we suggested that no long-lived aminyl radical species or copper-coordinated radical complex is formed in the amination pathway, though the mechanism of the reaction remains to be elucidated.…”

Section: Scheme 5 Amine Scope Of Phosphonate Aminationmentioning

confidence: 96%

α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives

McDonald

Wang

2014

Synlett

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A direct approach to access important α-amino phosphonic acids and their derivatives through the formation of C-N bonds is described. Several α-amination reactions of phosphonates that involve electrophilic aminating agents are reviewed. A recent development is highlighted in which an acyclic or cyclic amine is introduced into the α-position of a phosphonate in one step through deprotonative formation of an α-zincate followed by copper-catalyzed amination with an O-acylhydroxylamine.

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Copper(i) catalysed cyclisation of unsaturated N-benzoyloxyamines: an aminohydroxylation via radicals

Abstract: A new catalytic aminohydroxylation via radicals has been developed leading to cyclic aminoalcohols.

Cited by 126 publications

References 12 publications

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Recent Developments in Methodology for the Direct Oxyamination of Olefins

Iron Catalyzed Asymmetric Oxyamination of Olefins

α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives

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