135822-92-3Relevant academic research and scientific papers
Two-Step Asymmetric Synthesis of Disubstituted N-Tosyl Aziridines Having 98-100% ee: Use of a Phosphazene Base
Solladie-Cavallo, Arlette,Roje, Marin,Welter, Richard,Sunjic, Vitomir
, p. 1409 - 1412 (2004)
Unknown diaryl (1-3) and alkyl-phenyl (4, 5) N-tosyl aziridines have been successfully synthesized from pure (R,R,R,SS)-(-)-sulfonium salt derived from Eliel's oxathiane, tosylimines 11a-f, and using a phosphazene base (EtP2) to gene
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
NHC ligand-enabled Ni-catalyzed reductive coupling of alkynes and imines using isopropanol as a reductant
Yao, Wei-Wei,Li, Ran,Li, Jiang-Fei,Sun, Juan,Ye, Mengchun
supporting information, p. 2240 - 2244 (2019/05/17)
A nickel-catalyzed reductive coupling of alkynes and imines using readily available isopropanol as the reducing agent was developed. The use of a sterically bulky and electron-rich carbene ligand (AnIPr) significantly promotes the reaction, providing various multi-substituted allylic amines in 23-89% yield and the corresponding chiral ligand (AnIPr-3) can afford the products in 51-95% ee.
Alkenyl Exchange of Allylamines via Nickel(0)-Catalyzed C-C Bond Cleavage
Fan, Chao,Lv, Xin-Yang,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 2889 - 2893 (2019/02/19)
A functional group exchange reaction between allylamines and alkenes via nickel-catalyzed C - C bond cleavage and formation was developed. This reaction provides a novel protocol, which does not require the use of unstable imine substrates, for the synthesis of allylamines, which are widely used in the production of fine chemicals, pharmaceuticals, and agrochemicals.
Verkade's Superbase as an Organocatalyst for the Strecker Reaction
Yang, Jian,Chatelet, Bastien,Ziarelli, Fabio,Dufaud, Véronique,Hérault, Damien,Martinez, Alexandre
supporting information, p. 6328 - 6332 (2018/11/23)
Proazaphosphatranes -Verkade's superbases- proved to be efficient organocatalysts for the Strecker reaction between protected imines and trimethylsilyl cyanide (TMSCN). Excellent to quantitative yields were reached and, compared to other systems, only low
Palladium-Catalyzed Direct Intramolecular C-N Bond Formation: Access to Multisubstituted Dihydropyrroles
Jiang, Bing,Meng, Fei-Fan,Liang, Qiu-Ju,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 914 - 917 (2017/02/26)
A palladium-catalyzed intramolecular amination of alkenes with retention of olefin functionalization was achieved under mild reaction conditions. In the presence of palladium catalyst, the tosyl-protected amine can directly couple with a double bond to provide versatile dihydropyrrole derivatives in moderate to excellent yields.
Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles
Yasukawa, Tomohiro,Kuremoto, Tatsuya,Miyamura, Hiroyuki,Kobayashi, Sh?
supporting information, p. 2716 - 2718 (2016/06/15)
Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.
Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene
Lu, Xun,Schneider, Uwe
supporting information, p. 12980 - 12983 (2016/11/09)
Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita-Baylis-Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.
Chemoselective Boron-Catalyzed Nucleophilic Activation of Carboxylic Acids for Mannich-Type Reactions
Morita, Yuya,Yamamoto, Tomohiro,Nagai, Hideoki,Shimizu, Yohei,Kanai, Motomu
supporting information, p. 7075 - 7078 (2015/06/25)
The carboxyl group (COOH) is an omnipresent functional group in organic molecules, and its direct catalytic activation represents an attractive synthetic method. Herein, we describe the first example of a direct catalytic nucleophilic activation of carbox
A General Method for Imine Formation Using B(OCH2CF3)3
Reeves, Jonathan T.,Visco, Michael D.,Marsini, Maurice A.,Grinberg, Nelu,Busacca, Carl A.,Mattson, Anita E.,Senanayake, Chris H.
supporting information, p. 2442 - 2445 (2015/05/27)
Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] was found to be a mild and general reagent for the formation of a variety of imines by condensation of amides or amines with carbonyl compounds. N-Sulfinyl, N-toluenesulfonyl,
