Direct amination of β-oxo esters

Fioravanti, Stefania; Morreale, Alberto; Pellacani, Lucio; Tardella, Paolo A.

doi:10.1016/s0040-4039(00)02200-0

Cited by 24 publications

(12 citation statements)

References 9 publications

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“…The expected aminated products were obtained in yields up to 50%; if R' = H the reaction led to the synthesis of gem-diaminated -oxo esters. On the contrary, -oxo amides (Scheme 31) can be monofunctionalized under the same conditions and the use of Oppolzer's sultame allows a 40% diastereoselectivity [60]. Hanessian et al treated similar arylsulfonyloxycarbamates with -dicarboxyl compounds and NaH as the base, at low temperature, thereby obtaining an unexpected alkoxyaminocarbonylation (Scheme 32) [61].…”

Section: Amination Of Active Methylene Compoundsmentioning

confidence: 99%

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Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

Pellacani¹,

Fioravanti²,

Tardella

2011

COC

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The purpose of this review is to illustrate the use of ethyl nosyloxycarbamate (NsONHCO(2)Et). This is a versatile aminating agent known for over 47 years and used to generate, in the presence of organic or inorganic bases under homogeneous conditions, a carbonyl nitrene, a reactive intermediate able to form new C-N or X-N bonds by electrophilic amination reaction of a remarkable variety of nucleophilic substrates. Interest in this reagent has been renewed most recently, during the past dozen years. Operating still in alkaline medium, but under generally heterogeneous conditions, has made possible new synthetic applications for the conjugate base of the same nosyloxycarbamate. These, developed mainly by our research group, allow to carry out direct syntheses of various nitrogenated compounds under mild conditions. The applications span from simple molecules to highly functionalized compounds and many new exciting regio- and stereoselective routes can be envisioned. In particular, it was possible to obtain aziridines containing a cornucopia of assorted functions and therefore able to provide access to more complex molecules under simple operational conditions by using an aminating agent cheap and easy to obtain

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Section: Amination Of Active Methylene Compoundsmentioning

confidence: 99%

“…2,4 ]octanes (Scheme 10) [33], and [60]fullero aziridines (Scheme 11) [34,35] were prepared. In the last case also oxazolidin-2-one derivatives were formed.…”

Section: Introductionmentioning

confidence: 99%

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

Pellacani¹,

Fioravanti²,

Tardella

2011

COC

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“…Since then this method of amination has evolved and currently has different forms as well as different applications [3][4][5][6][7]. In this paper, the direct amination method relies on electrophilic substitution of the onium ion (NH=N + =NH or N≡N + NH 2 ), which is a protonated form of hydrazoic acid.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of alkylcarbazole aminoderivatives

Garman

Olewnik

Czerwiński

2011

Heteroatom Chemistry

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“…Good results have been observed when using α-nitro olefins and several olefins that carry two geminal electron-withdrawing groups. [6] Inversely, the amination of fumarates and maleates does not proceed as satisfactorily under a variety of conditions. [7] tert-Butyl arylsulfonyloxycarbamates (ArSO 3 NHCO 2 -tBu) undergo aza-MIRC reactions with electron-poor olefins, but electrophilic amination reactions have rarely been between these olefins and the aminating agents.…”

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Aza‐MIRC Reactions of Sulfonyl‐Activated Hydroxycarbamates with α,β‐Difunctionalised Acrylates

et al. 2003

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Highly functionalised aziridines are readily obtained in high yields (up to 95%) under mild conditions from the reaction of trisubstituted olefins bearing different groups with nosyloxycarbamates in the presence of calcium oxide. We propose a possible explanation for the different reactivities observed between these olefins and the aminating agents. Reagent‐controlled stereoselective amination reactions led to the expected products with high conversions and purities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Direct amination of β-oxo esters

Cited by 24 publications

References 9 publications

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

Ethyl Nosyloxycarbamate: A Chameleonic Aminating Agent

Synthesis of alkylcarbazole aminoderivatives

Aza‐MIRC Reactions of Sulfonyl‐Activated Hydroxycarbamates with α,β‐Difunctionalised Acrylates

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