20020-75-1Relevant academic research and scientific papers
Stereoselective and Enantiospecific Mono- and Bis-C?H Azidation of Tr?ger Bases: Insight on Bridgehead Iminium Intermediates and Application to Anion-Binding Catalysis
Bosmani, Alessandro,Pujari, Sandip A.,Besnard, Céline,Guénée, Laure,Poblador-Bahamonde, Amalia I.,Lacour, Jér?me
, p. 8678 - 8684 (2017)
In the context of Tr?ger base chemistry, regio- and stereoselective Csp3?H azidation reactions are reported. Azide functional groups are introduced at either one or the two benzylic positions selectively. Mild conditions and good yields are aff
Pyrrole-Based Anion-Responsive π-Electronic Molecules as Hydrogen-Bonding Catalysts
Hirata, Goki,Maeda, Hiromitsu
supporting information, p. 2853 - 2856 (2018/05/29)
The abilities of dipyrrolyldiketone boron complexes as hydrogen-bonding donor organocatalysts were examined by the Mannich-type reaction of N-acyl heteroarenium chlorides with 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene, as well as by the classical N-alkylation of amines with trityl chloride under base-free conditions. 1H NMR examinations of the hydrogen-bonding interaction between the pyrrole NH of the catalyst and the Cl- in the N-acyl heteroarenium salt suggested that the activation of N-acyl heteroarenium chlorides occurs through anion binding by the catalyst.
Straightforward synthesis and antioxidant studies of chalcogenoaziridines
Borges, Rodrigo,Andrade, Floyd C.D.,Schwab, Ricardo S.,Sousa, Fernanda S.S.,de Souza, Maurice Neto,Savegnago, Lucielli,Schneider, Paulo H.
, p. 3501 - 3504 (2016/07/15)
Herein we reported the synthesis of chalcogenoaziridines through the introduction of the organoselenium moiety in the aziridine framework through the nucleophilic substitution of the OTs leaving group. In addition, the antioxidant activity, as reflected b
"Click" bis-triazoles as neutral C-H?anion-acceptor organocatalysts
Beckendorf, Stephan,Asmus, S?ren,Mück-Lichtenfeld, Christian,García Manche?o, Olga
supporting information, p. 1581 - 1585 (2013/03/14)
A new player on the field! "Click" bis-triazoles have been introduced as a highly efficient new class of neutral C-H?anion-binding organocatalysts (see scheme). DFT and NMR studies were used to confirm this activation modus and identify the optimal catalyst. Copyright
N-allylideneamines derived from acrolein: synthesis and use as acceptors of two nucleophiles
Mizota, Isao,Matsuda, Yuri,Hachiya, Iwao,Shimizu, Makoto
scheme or table, p. 4073 - 4084 (2009/12/26)
Two practical methods have been developed for the preparation of N-allylideneamines 1b,c. One involves the isomerlzation of propargylamines and the other the dehydration of acrolein. N-Allylideneamines 1b,c thus prepared, were used as efficient substrates
Investigation of a flexible enantiospecific approach to aziridines
Jamookeeah, Clare E.,Beadle, Christopher D.,Jackson, Richard F. W.,Harrity, Joseph P. A.
, p. 1128 - 1130 (2008/09/18)
(Chemical Equation Presented) A flexible approach to functionalized and enantioenriched aziridines has been developed from an intermediate aziridinylmethyl tosylate. This protocol features a Cu-catalyzed Grignard substitution reaction that allows a range of functionalized organic fragments to be incorporated. Moreover, a convenient one-pot procedure is outlined that allows the trityl group to be exchanged for a range of common N-protecting groups.
A convenient method for the preparation of primary amines using tritylamine
Theodorou, Vassiliki,Ragoussis, Valentine,Strongilos, Alexandros,Zelepos, Evangelos,Eleftheriou, Argyro,Dimitriou, Maria
, p. 1357 - 1360 (2007/10/03)
A simple method for the preparation of primary amines by treating N-tritylamines with trifluoroacetic acid has been established. The N-tritylamines were prepared by the reaction of alkyl halides or alkyl p-toluenesulfonates with tritylamine, or by the reaction of alkyl bromides with lithium tritylamide.
Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry
Pepito, Aurora S.,Dittmer, Donald C.
, p. 7920 - 7925 (2007/10/03)
Sulfonate esters of aziridinemethanols are converted to allylic amines by treatment with telluride ion obtained by reduction of elemental tellurium. In the course of the reaction, tellurium(0) is reformed and may be reused, thus removing the need to dispose of a key reagent. The telluride reaction yields optically active allylic amines from optically active aziridinemethanols. In contrast to many ring-openings of aziridines by nucleophiles, activation by an electron-withdrawing substituent on nitrogen is not necessary and is even detrimental.
