- Urethanes synthesis from oxamic acids under electrochemical conditions
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Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.
- Ogbu, Ikechukwu Martin,Lusseau, Jonathan,Kurtay, Gülbin,Robert, Frédéric,Landais, Yannick
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supporting information
p. 12226 - 12229
(2020/10/26)
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- Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates
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A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is
- Liu, Shuai,Achou, Rapha?l,Boulanger, Coline,Pawar, Govind,Kumar, Nivesh,Lusseau, Jonathan,Robert, Frédéric,Landais, Yannick
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supporting information
p. 13013 - 13016
(2020/11/05)
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- Dynamic kinetic resolution of amines by using palladium nanoparticles confined inside the cages of amine-modified MIL-101 and lipase
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Dynamic kinetic resolution (DKR) of amines is an important strategy for the synthesis of chiral drugs and their building blocks; however, improving the matchability of metal-catalyzed racemization and enzymatic resolution is still a task. In this paper, P
- Xu, Sen,Wang, Meng,Feng, Bo,Han, Xinchen,Lan, Zijie,Gu, Huajun,Li, Hexing,Li, Hui
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- L-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate
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The reaction of amines and dimethyl carbonate (DMC) in the presence of catalytic amounts of l-proline and tetrabutylammonium bromide (TBAB) afforded methyl carbamates in good to excellent yields under mild conditions. The presence of both l-proline and TBAB co-catalysts is vital for this transformation.
- Kumar, Subodh,Jain, Suman L.
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p. 2935 - 2938
(2013/09/12)
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- Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography
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Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.
- Nakamura, Tsuyoshi,Tateishi, Kaori,Tsukagoshi, Shiori,Hashimoto, Saori,Watanabe, Shotaro,Soloshonok, Vadim A.,Ace?a, José Luis,Kitagawa, Osamu
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experimental part
p. 4013 - 4017
(2012/07/14)
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- Aluminum triflate as a powerful catalyst for direct amination of alcohols, including electron-withdrawing group-substituted benzhydrols
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Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron-withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo-substituted product was further transformed into letrozole. Copyright
- Ohshima, Takashi,Ipposhi, Junji,Nakahara, Yasuhito,Shibuya, Ryozo,Mashima, Kazushi
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supporting information
p. 2447 - 2452
(2012/11/07)
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- Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups
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We developed a simple, efficient, and selective method for preparing organic carbamates and carbonates using a catalytic amount of indium. A wide range of carbamates and carbonates were synthesized in high yields. The method is also applicable to the selective protection of amino groups under mild conditions.
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 2688 - 2692
(2009/08/09)
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- Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines
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The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.
- Denmark, Scott E.,Nakajima, Noriyuki,Stiff, Cory M.,Nicaise, Olivier J.-C.,Kranz, Michael
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supporting information; experimental part
p. 1023 - 1045
(2009/05/30)
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- Mild and convenient synthesis of organic carbamates from amines and carbon dioxide using tetraethylammonium superoxide
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A safe and simple method of preparing organic carbamates has been achieved from amines and carbon dioxide using tetraethylammonium superoxide generated in situ. Copyright Taylor & Francis Group, LLC.
- Singh, Krishna Nand
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p. 2651 - 2654
(2008/02/12)
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- Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis
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A facile synthesis of carbamates from amines and dimethyl carbonate has been achieved using ytterbium triflate as catalyst.
- Curini, Massimo,Epifano, Francesco,Maltese, Federica,Rosati, Ornelio
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p. 4895 - 4897
(2007/10/03)
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- Lewis acid-catalyzed reductive amination of carbonyl compounds with aminohydrosilanes
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The TiCl4-catalyzed reaction of aromatic carbonyl compounds with (dialkylamino)dimethylsilanes gave tertiary amines in moderate to high yields. The reductive amination of aliphatic aldehydes was effectively catalyzed by ZnI2. Methyl
- Miura,Ootsuka,Suda,Nishikori,Hosomi
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p. 1617 - 1619
(2007/10/03)
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- An environmentally benign access to carbamates and ureas
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Ureas were synthesized from methyl carbamates which were obtained by reaction of amines with dimethylcarbonate. Both reactions were catalyzed by γ-A12O3. (C) 2000 Elsevier Science Ltd.
- Vauthey,Valot,Gozzi,Fache,Lemaire
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p. 6347 - 6350
(2007/10/03)
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- A practical procedure for the preparation of carbamates from azides
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A practical procedure for the direct conversion of azides to carbamates has been found. High yields are obtained when primary and secondary aliphatic azides, as well as α-azido esters, are treated in THF with Me3P and several chloroformates (ClCOOBn, ClCOOMe, ClCOOEt, ClCOOCH2CCl3, ClCOOCH2CH=CH2).
- Ariza, Xavier,Urpi, Felix,Vilarrasa, Jaume
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p. 7515 - 7517
(2007/10/03)
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- Homochiral Amine Synthesis by Baker's Yeast Resolution of a β-Keto Amide: 1-Phenylethylamine
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Preliminary investigation of the resolution potential of baker's yeast reduction of β-keto amides has been carried out with 1-phenylethylamine.Enantiomeric excess was determined by direct comparison of resolved enantiomers with derivatives prepared from c
- Hudlicky, T.,Gillman, Gene,Andersen, Catherine
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p. 281 - 286
(2007/10/02)
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