- A general method for deprotection of N-toluenesulfonyl aziridines using sodium naphthalenide
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Deprotection of a variety of N-tosylaziridines with sodium naphthalenide provided the corresponding N-H-aziridines in excellent yield. No single electron transfer (SET) induced aziridine ring opening was seen under the conditions employed for the deprotection reaction.
- Bergmeier, Stephen C.,Seth, Punit P.
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- Copper-catalyzed ring-opening reactions of alkyl aziridines with b2 pin2: Experimental and computational studies
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The possibility to form new C–B bonds with aziridines using diboron derivatives con-tinues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individua-tion of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2 pin2 ) in a regioselective nucleophilic addition reaction under copper catalysis.
- Boldrini, Cosimo,Comparini, Lucrezia Margherita,Di Bussolo, Valeria,Di Pietro, Sebastiano,Favero, Lucilla,Menichetti, Andrea,Pineschi, Mauro
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supporting information
(2021/12/17)
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- Benzphetamine hydrochloride preparation method
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The invention relates to the field of chemical pharmacy, particularly to a benzphetamine hydrochloride preparation method. According to the invention, the method avoids the use of ephedrine, pseudoephedrine, deoxyephedrine and other management and control products, has characteristics of inexpensive and easily-available raw materials and synthesis cost reducing, can obtain the high-purity target compound at high yield, and is suitable for industrial large-scale production.
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Paragraph 0090; 0097; 0098; 0099; 0100; 0101; 0102
(2020/01/25)
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- Observations on the modified wenker synthesis of aziridines and the development of a biphasic system
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A cheap and reliable process for the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions for a range of amino alcohol starting materials. A 100 mmol "one-pot" process has also been devised, and the enantiopurity of the starting amino alcohol is retained in the aziridine product.
- Buckley, Benjamin R.,Patel, Anish P.,Wijayantha
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p. 1289 - 1292
(2013/04/10)
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- Addition reactions of chloro- Or iodomethyllithium to imines. Synthesis of enantiopure aziridines and β-chloroamines
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We report a novel, simple, and efficient synthesis of aziridines and l-chloroalkan-2-amines by the reaction of imines derived from various aldehydes and p-toluenesulfonamide or benzenesulfonamide with iodoor chloromethyllithium, respectively. Both halogenated anions were generated in situ by treatment of diiodo- or chloroiodomethane with methyllithium at -78 or 0 °C. The reaction of in situ generated iodoor chloromethyllithium could also be performed from chiral 2-aminoaldimines to yield enantiopure aziridines or (2S,3S)-2,3-diamino- l-chloroalkanes with high stereoselectivity.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Bernad, Pablo L.,Simal, Carmen
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supporting information; experimental part
p. 2452 - 2459
(2009/07/18)
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- Instantaneous deprotection of tosylamides and esters with Sml 2/amine/water
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(Chemical Equation Presented) Sml2/amine/water mediates instantaneous cleavage of tosyl amides and tosyl esters. Highly hindered, sensitive and functionalized substrates were successfully deprotected in near quantitative yield.
- Ankner, Tobias,Hilmersson, Goeran
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supporting information; scheme or table
p. 503 - 506
(2009/07/11)
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- Addition reactions of iodomethyllithium to imines. A direct and efficient synthesis of aziridines and enantiopure amino aziridines
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(Chemical Equation Presented) An efficient and general synthesis of aziridines by the reaction of imines derived from p-toluenesulfonamides with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, is reported for the first time. The reaction with the chiral aldimine derived from phenylalaninal allowed access to (2R,1′S)-2-(1′-aminoalkyl) aziridine with very high diastereoselectivity, in enantiopure form. A mechanism to explain this novel reaction is proposed.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Simal, Carmen
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supporting information; experimental part
p. 4457 - 4460
(2009/05/07)
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- Alkali metals in silica gel (M-SG): A new reagent for desulfonation of amines
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(Chemical Equation Presented) A novel method for the desulfonation of secondary amines is described. Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful solid-state reagents for the desuffonation of a range of N,N-disubstituted sulfonamides. M-SG reagents are room-temperature- stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.
- Nandi, Partha,Redko, Mikhail Y.,Petersen, Kathryn,Dye, James L.,Lefenfeld, Michael,Vogt, Paul F.,Jackson, James E.
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supporting information; experimental part
p. 5441 - 5444
(2009/06/18)
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