An efficient method for opening N -tosylaziridines with silylated nucleophiles by using polystyrene-supported 1,5,7-triazabicyclo[44.0]dec-5-ene as a reusable organocatalyst
Polystyrene-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (PS-TBD) catalyzes the ring opening of N-tosylaziridines with trimethylsilyl cyanide, trimethylsilyl azide, or trimethylsilyl halides to give the corresponding products in high yields. PS-TBD can b
Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles
Polystyrene-supported TBD (PS-TBD) catalyzes the ring-opening of N-tosylaziridines with silylated nucleophiles to give the corresponding products in high yields. PS-TBD was easily recovered and reused without significant loss of catalytic activity.
Matsukawa, Satoru,Harada, Takeru,Yasuda, Shiori
supporting information; experimental part
p. 4886 - 4890
(2012/07/27)
SN2-type ring opening of substituted-N-tosylaziridines with zinc (II) halides: Control of racemization by quaternary ammonium salt
Quaternary ammonium salt mediated highly regioselective ring opening of aziridines with zinc(II) halides to racemic and non-racemic β-halo amines in excellent yield and selectivity is described. The reaction proceeds via an SN2-type pathway and
Ghorai, Manas K,Tiwari, Deo Prakash,Kumar, Amit,Das, Kalpataru
experimental part
p. 951 - 961
(2012/03/08)
PPh3/halogenating agent-mediated highly efficient ring opening of activated and non-activated aziridines
We report here the use of PPh3/halogenating agents as highly efficient reagents for the ring opening of aziridines with halides. The method works effectively for both activated and non-activated aziridines, and furnishes the products in excelle
Kumar, Manoj,Pandey, Sanjay K.,Gandhi, Shikha,Singh, Vinod K.
scheme or table
p. 363 - 365
(2009/04/19)
Lewis base catalyzed ring opening of aziridines with silylated nucleophiles
(Chemical Equation Presented) The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N′,N′- tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regi
An efficient route to regioselective opening of N-tosylaziridines with zinc(II) halides
An efficient route for the regio- and stereoselective ring opening of N-tosylaziridines with zinc dihalides (ZnX2, X = Cl, Br, I) is described. Depending on the solvent and Zn(II) halide, β-halo amines or imidazolines are obtained selectively in good to excellent yields.
Regioselective ring opening of aziridines with activated DMF complexes: A facile synthesis of β-haloamines
A wide variety of aziridines were converted to the corresponding β-haloamines using activated DMF complexes in good to excellent yields with high regioselectivity.
Pandey, Manoj K.,Bisai, Alakesh,Singh, Vinod K.
p. 9661 - 9663
(2007/10/03)
Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation
The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
p. 721 - 725
(2007/10/02)
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