817209-02-2Relevant articles and documents
Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
, p. 3722 - 3728 (2021)
N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
, p. 7540 - 7544 (2021/10/12)
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
Bicyclic Bridgehead Phosphoramidite-Based Hybrid Diphosphorus Ligands: Design, Synthesis, and Application in Catalytic Asymmetric Hydrogenation
Du, Hong-Quan,Hu, Xiang-Ping
supporting information, p. 7678 - 7682 (2021/10/12)
A strategy for chiral ligand design has been developed that allows for incorporation of an achiral bicyclic bridgehead phosphoramidite to generate a class of hybrid diphosphorus ligands for high activity and asymmetric control. Using this concept, a series of chiral phosphine-phosphoramidite ligands bearing the sole chirality at the ligand backbone have been prepared and successfully employed in the Rh-catalyzed asymmetric hydrogenation of 2-vinylanilides for the synthesis of optically active anilines bearing an ortho-tertiary benzylic stereocenter.
Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides
Whyte, Andrew,Torelli, Alexa,Mirabi, Bijan,Lautens, Mark
supporting information, p. 8373 - 8377 (2019/10/14)
An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.
Enantioselective Intramolecular Copper-Catalyzed Borylacylation
Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
supporting information, p. 13927 - 13930 (2018/10/02)
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
Palladium-Catalyzed Domino Alkenylation/Amination/Pyridination Reactions of 2-Vinylanilines with Alkynes: Access to Cyclopentaquinolines
Li, Dejun,Zeng, Fanlong
, p. 6498 - 6501 (2017/12/26)
A novel domino oxidative annulation of 2-vinylanilines with internal alkynes was developed to constitute a rare class of cyclopentaquinoline derivatives. This transformation encompasses four σ bonds formation, one quaternary carbon center construction, and pyridination steps in one pot under identical conditions, which fascinatingly increases the molecular complexity from easily available starting materials.
Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
Huang, Ya-Nan,Li, Yin-Long,Li, Jian,Deng, Jun
, p. 4645 - 4653 (2016/07/06)
A novel rapid synthesis of quinolines from 2-alkenylanilines has been described; the reaction involves an unexpected DMAP-catalyzed cyclization of 2-alkenylanilines with di-tert-butyl dicarbonate (Boc2O, 2.0 equiv), and a series of tert-butyl quinolin-2-yl carbonate with various functional groups have been synthesized in good yields under mild conditions. Furthermore, the tert-butyl quinolin-2-yl carbonate can be easily converted into corresponding quinolinones and 2-(pseudo)haloquinolines.
Titanium-imido complexes with pendant groups- Synthesis, characterization, and evaluation of their role as precatalysts for ethylene polymerization
Nguyen, Viet-Hoang,Vendier, Laure,Etienne, Michel,Despagnet-Ayoub, Emmanuelle,Breuil, Pierre-Alain R.,Magna, Lionel,Proriol, David,Olivier-Bourbigou, Helene,Lorber, Christian
scheme or table, p. 97 - 111 (2012/03/13)
The synthesis of several anilines (ArPGNH2) substituted in the ortho position with pendant groups (PGs, terminated by potentially coordinative arene, thienyl, furanyl, or pyridyl functionalities) was accomplished by a two- to five-st
