- Lewis acids promoted 3 + 2 cycloaddition of oxaziridines and cyclic allylic alcohols through carbonyl imine intermediates
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Syntheses of isoxazolidines through the carbonyl imine intermediates are currently limited to monosubstituted olefin substrates. Herein, we reported syntheses of novel bicyclic isoxazolidine-containing compounds through 1,3-dipolar cycloaddition reactions
- Zhao, Erbao,Zhou, Feilong,Zhao, Yujun
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p. 4282 - 4293
(2019/04/30)
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- Oxaziridinium compound (by machine translation)
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Various applications such as various reaction using compound [a] oxidant oxaziridines, safe and simple, while eliminating as much as possible intrusion of impurities which can be efficiently manufactured oxaziridinium compound production method. The follo
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- Novel chiral thiourea organocatalysts for the catalytic asymmetric oxaziridination
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Catalytic enantioselective oxaziridination is one of the challenging reactions in the oxidation of organic molecules. In this article, a series of novel chiral thiourea moleculars were synthesized from natural cinchona alkaloids and primary amines. By usi
- Ji, Nan,Yuan, Jiani,Xue, Shanshan,Zhang, Junna,He, Wei
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supporting information
p. 512 - 517
(2015/12/31)
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- Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights
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A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.
- Ghosh, Asit,Mandal, Subhajit,Chattaraj, Pratim Kumar,Banerjee, Prabal
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supporting information
p. 4940 - 4943
(2016/10/18)
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- Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes
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A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.
- Kra?em, Jamil,Ghedira, Donia,Ollevier, Thierry
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p. 4859 - 4864
(2016/10/12)
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- Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters
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An efficient kinetic resolution of racemic oxaziridines has been realized via catalytic asymmetric α-hydroxylation of available β-keto esters. In the presence of a chiral bifunctional guanidine catalyst, a variety of optically active oxaziridines and chir
- Lin, Xiaobin,Ruan, Sai,Yao, Qian,Yin, Chengkai,Lin, Lili,Feng, Xiaoming,Liu, Xiaohua
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supporting information
p. 3602 - 3605
(2016/08/16)
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- Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines
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A highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high d.r., yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
- Smith, Siobhan R.,Fallan, Charlene,Taylor, James E.,McLennan, Ross,Daniels, David S. B.,Morrill, Louis C.,Slawin, Alexandra M. Z.,Smith, Andrew D.
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supporting information
p. 10530 - 10536
(2015/07/07)
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- Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines
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We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.
- Williamson, Kevin S.,Sawicki, James W.,Yoon, Tehshik P.
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p. 3524 - 3527
(2014/08/18)
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- Racemic N-sulfonyloxaziridines as highly diastereoselective enolate hydroxylating agents: Enantioselective synthesis of (2S,3S)-3-amino-N- cyclopropyl-2-hydroxyhexanamide
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A new, highly enantioselective synthesis of (2S,3S)-3-amino-N-cyclopropyl- 2-hydroxyhexanamide, a synthetic fragment of the experimental hepatitis C drug Telaprevir, has been described. Conjugate addition of the enantiomerically pure Davies lithium amide
- Kiss, Eleonóra,Markó, István E.,Guillaume, Michel
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p. 9173 - 9178
(2011/12/01)
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- Iron(II)-catalyzed amidation of aldehydes with iminoiodinanes at room temperature and under microwave-assisted conditions
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A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C-H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)4Cl2] generated in situ from reaction of FeCl 2 with pyridine.
- Ton, Thi My Uyen,Tejo, Ciputra,Tania, Stefani,Chang, Joyce Wei Wei,Chan, Philip Wai Hong
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p. 4894 - 4904
(2011/08/03)
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- Practical copper(I)-catalysed amidation of aldehydes
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The direct synthesis of amides by insertion into the C-H bond of aldehydes is shown to be a practical procedure through application of cheap, readily available catalysts generated in situ from copper(i) halides and pyridine. The Royal Society of Chemistry 2010.
- Chang, Joyce Wei Wei,Ton, Thi My Uyen,Tania, Stefani,Taylor, Paul C.,Chan, Philip Wai Hong
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supporting information; experimental part
p. 922 - 924
(2010/06/12)
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- UREIDE DERIVATIVE AND USE THEREOF FOR MEDICAL PURPOSES
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This invention relates to a pharmaceutical comprising, as an active ingredient, a ureide derivative represented by formula: or a pharmaceutically acceptable salt thereof. The ureide derivative or a pharmaceutically acceptable salt thereof according to the present invention is useful for relieving pain and treating or preventing neuropathic pain.
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- A new general method for the preparation of N-sulfonyloxaziridines
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(Chemical Equation Presented) A simple procedure to obtain N-alkylsulfonyl- and N-arylsulfonyloxaziridines from the corresponding N-sulfinylimines involving a one-pot, two-step oxidation process with m-CPBA (1 equiv) and m-CPBA/KOH (1.1 equiv) is reported
- Garcia Ruano, Jose Luis,Aleman, Jose,Fajardo, Cristina,Parra, Alejandro
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p. 5493 - 5496
(2007/10/03)
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- Chemistry of Oxaziridines. 1. Synthesis and Structure of 2-Arenesulfonyl-3-aryloxaziridines. A New Class of Oxaziridines
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A new class of oxaziridine derivatives, 2-arenesulfonyl-3-aryloxaziridines (2), is prepared by m-CPBA oxidation of sulfonimines (RSO2N=CHAr).These compounds are the first stable examples of this ring system to have a substituent other than carbon attached to nitrogen and are characterized by a highly electrophilic oxaziridine oxygen atom.These oxaziridines have the E configuration as determined by X-ray crystallography.The presence of the powerful electron-attracting sulfonyl group attached to nitrogen apparently has little effect on the structure of the oxaziridine three-membered ring.Of more significance are the observations that the nitrogen lone pair in 2 is opposite to one of the sulfonyl oxygens and that the long S-N bond length implies little if any conjugative interaction between sulfur and nitrogen.Attempts to prepare oxaziridines via oxidation of sulfonimines, 5, derived from acetophenone gave imidoyl ether 14, a novel Baeyer-Villiger oxidation product of a C-N double bond.
- Davis, Franklin A.,Lamendola, Joseph,Nadir, Upender,Kluger, Edward W.,Sedergran, Thomas C.,et al.
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p. 2000 - 2005
(2007/10/02)
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