Search results

Search for "oxyamination" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

  • Akanksha Chhikara,
  • Fan Wu,
  • Navdeep Kaur,
  • Prabagar Baskaran,
  • Alex M. Nguyen,
  • Zhichang Yin,
  • Anthony H. Pham and
  • Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

Graphical Abstract
  • ; lithium salt activation; olefin oxyamination; oxazoline; Introduction Hypervalent iodine(III) reagents, also known as λ3–iodanes, have been well established and used in organic synthesis for the past decades [1][2][3][4][5]. The pioneering works of Fuchigami and Fugita, Ochiai, Kita, and later the
  • ]. Notably, an interesting work by Hashimoto has recently enabled the intermolecular addition of N-(fluorosulfonyl)-protected carbamates as oxyamination reagents across a variety of olefin structures [47]. This work engages the hypervalent iodine catalyst in an anionic ligand exchange with the substrate
  • hypervalent iodine catalyst. The cationic hypervalent iodine catalyst could then activate the olefin to allow the addition of bifunctional nucleophiles such as an amide to achieve an overall olefin oxyamination process. We have previously reported a series of iodide-catalyzed processes, in which the
PDF
Album
Supp Info
Letter
Published 24 Jun 2024

Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates

  • Ekta Gupta,
  • Narendra Kumar Vaishanv,
  • Sandeep Kumar,
  • Raja Krishnan Purshottam,
  • Ruchir Kant and
  • Kishor Mohanan

Beilstein J. Org. Chem. 2022, 18, 217–224, doi:10.3762/bjoc.18.25

Graphical Abstract
  • ). The disubstituted malonamates underwent facile oxyamination, and the products were obtained in excellent yields and enantioselectivities (4k, 4l). Of note, the reaction was also feasible with heterocyclic malonamate, albeit with moderate yield and enantioselectivity (4m). Aliphatic malonamate was also
PDF
Album
Supp Info
Letter
Published 21 Feb 2022

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration–oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles

  • Lívia Dikošová,
  • Júlia Laceková,
  • Ondrej Záborský and
  • Róbert Fischer

Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112

Graphical Abstract
  • substitution reactions of properly substituted hydroxylamines [19][20] and N-hydroxyphthalimides [21][22][23][24] as well as by Tamao oxidations of 4-silylisoxazolidines [25][26]. Very recently, Tomkinson et al. described a simple and effective method for an intramolecular oxyamination of allylic N-tosyl
PDF
Album
Supp Info
Full Research Paper
Published 16 Jun 2020

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

Graphical Abstract
  • 2009, Jang’s group disclosed the first example of the anodic oxidation of enamines (SOMO protocol) in terms of asymmetric α-oxyamination of aldehydes [74]. Galvanostatic electrolysis of aldehydes 105 in a single compartment cell using TEMPO (106) in presence of chiral secondary amine catalyst 107
PDF
Album
Review
Published 13 Nov 2019

Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions

  • Nicholas L. Reed,
  • Madeline I. Herman,
  • Vladimir P. Miltchev and
  • Tehshik P. Yoon

Beilstein J. Org. Chem. 2019, 15, 351–356, doi:10.3762/bjoc.15.30

Graphical Abstract
  • describe a method for alkene oxyamination and diamination that utilizes simple carbamate and urea groups as nucleophilic heteroatom donors. This method uses a tandem copper–photoredox catalyst system that is operationally convenient. The identity of the terminal oxidant is critical in these studies. Ag(I
  • ) salts proved to be unique in their ability to turn over the copper cocatalyst without deleteriously impacting the reactivity of the organoradical intermediates. Keywords: copper; diamination; oxidative functionalization; oxyamination; photoredox catalysis; radical; Introduction Over the past decade, a
  • combines the photoredox activation of electron-rich alkenes with copper(II)-mediated oxidation of electron-rich radicals as described by Kochi [18][19][20]. These studies resulted in the development of a general new protocol for oxyamination (Figure 1a) and diamination (Figure 1b) of alkenes. The mechanism
PDF
Album
Supp Info
Letter
Published 05 Feb 2019

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

  • Soumen Ghosh,
  • Suman Pradhan and
  • Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

Graphical Abstract
  • formation and ring opening of aziridinium intermediate 58 elucidate the product formation in this transformation [51]. Wirth et al. successfully employed I(III) reagent 8b in combination with trimethylsilyltriflate (TMSOTf) for the stereoselective oxyamination of 59 to furnish isourea 60 with >99% ee
  • diamination of alkenes. Stereoselective oxyamination of alkenes reported by Wirth et al. Enantioselective and regioselective aminofluorination by Nevado et al. Fluorinated difunctionalization reported by Jacobsen et al. Aryl rearrangement reported by Wirth et al. α-Arylation of β-ketoesters. Asymmetric α
PDF
Album
Review
Published 30 May 2018

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

  • Brett N. Hemric and
  • Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

Graphical Abstract
  • Brett N. Hemric Qiu Wang Department of Chemistry, Duke University, Durham, NC, USA 10.3762/bjoc.12.4 Abstract This paper reports a novel approach for the direct and facile synthesis of 1,2-oxyamino moieties via an intermolecular copper-catalyzed oxyamination of olefins. This strategy utilizes O
  • . Keywords: copper; electrophilic amination; olefin oxyamination; Introduction The 1,2-oxyamino motif is highly valuable and found in a vast range of biologically active natural products, pharmaceuticals, and agrochemicals (Figure 1) [1][2]. Representative examples include salmeterol (Advair®), a β2
  • class of molecules is highly valued. Toward this end, intermolecular olefin oxyamination allows for direct and modular installation of both oxygen and amino groups to readily available olefins in a single step, representing a powerful and appealing approach over multistep sequences [7][8][9]. Sharpless
PDF
Album
Supp Info
Letter
Published 07 Jan 2016

Enantioselective total synthesis of (R)-(−)-complanine

  • Krystal A. D. Kamanos and
  • Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

Graphical Abstract
  • complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product. Keywords: complanine; enantioselective synthesis; marine fireworm; nitrosoaldol
PDF
Album
Full Research Paper
Published 04 Oct 2012

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

  • Kengo Akagawa,
  • Ryota Umezawa and
  • Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

Graphical Abstract
  • –Crafts-type alkylation of α,β-unsaturated aldehydes followed by an α-oxyamination was realized. The reaction in aqueous solvent to promote the enzymatic oxidation, and the use of a peptide catalyst compatible with such conditions, were essential. The present sequential reaction afforded oxygen
  • -functionalized indole or pyrrole derivatives in a highly enantioselective manner. Keywords: Friedel–Crafts-type alkylation; laccase; one-pot reaction; organocatalysis; α-oxyamination; resin-supported peptide catalyst; Findings Indole derivatives represent a class of biologically active compounds [1][2][3], and
  • FCAA reaction toward α,β-unsaturated aldehydes through iminium intermediates [32][37], and an asymmetric α-oxyamination of aldehydes via enamines [33], they are expected to be suitable for a one-pot sequential reaction to make the chiral indoles mentioned above. Herein, we report on an enantioselective
PDF
Album
Supp Info
Letter
Published 17 Aug 2012
Other Beilstein-Institut Open Science Activities