360065-87-8Relevant academic research and scientific papers
Palladium-catalysed nucleophilic release of allylic amines from a phenolic resin
Fisher, Martyn,Brown, Richard C.D
, p. 8227 - 8230 (2001)
2° Allylic alcohols were coupled to phenolic polystyrene resin under Mitsunobu conditions to provide substituted allyl ethers, which underwent efficient nucleophilic cleavage by 1° and 2° amines in the presence of catalytic palladium to afford allylic amines.
Intramolecular [2 + 2] and [4 + 2] Cycloaddition Reactions of Cinnamylamides of Ethenetricarboxylate in Sequential Processes
Yamazaki, Shoko,Sugiura, Hirotaka,Ohashi, Shinnosuke,Ishizuka, Keisuke,Saimu, Rina,Mikata, Yuji,Ogawa, Akiya
, p. 10863 - 10886 (2016)
Intramolecular [2 + 2] and [4 + 2] cycloaddition reactions of cinnamylamides of ethenetricarboxylate in sequential processes have been studied. Reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and trans-cinnamylamines in the presence of EDCI/HOBt/Et3N led to pyrrolidine products in one pot, via intramolecular [2 + 2], [4 + 2], and some other cyclizations. The types of the products depend on the substituents on the benzene ring and the reaction conditions. Reaction of cinnamylamines without substituents on the benzene ring and with halogens and OMe on the para position at room temperature gave cyclobutane-fused pyrrolidines as major products via [2 + 2] cycloaddition. The reaction at 80 °C in 1,2-dichloroethane gave δ-lactone fused pyrrolidines as major products, probably via ring-opening of the cyclobutanes. Interestingly, reaction of 1,1-diethyl 2-hydrogen ethenetricarboxylate and cinnamylamines bearing electron-withdrawing groups such as NO2, CN, CO2Me, CO2Et, and CF3 on ortho and para positions in the presence of EDCI/HOBt/Et3N at room temperature or at 60-80 °C gave tetrahydrobenz[f]isoindolines via [4 + 2] cycloaddition as major products. DFT studies have been performed to explained the observed [2 + 2]/[4 + 2] selectivity.
Solid-phase synthesis of 4-methylene pyrrolidines and allylic amines using palladium-activated allylic linkers
Brown, Richard C.D.,Fisher, Martyn L.,Brown, Lynda J.
, p. 2699 - 2709 (2007/10/03)
The solid-phase synthesis of 4-methylene pyrrolidines and allylic amines has been achieved using palladium-catalysed nucleophilic cleavage of allylic linkages. Six pyrrolidines were synthesised in five steps from a carboxyethyl resin 20, where the key transformations included a Lewis-acid promoted imino-Sakurai type reaction and reductive alkylation prior to the final palladium-catalysed cyclisation cleavage of the allylic carboxylate linkage. Allylic carboxylate resin 22 was also shown to undergo "traceless" cleavage using various hydride sources in the presence of catalytic palladium. A more robust allylic ether linkage was also investigated. Starting from a phenol resin 36, a number of 3-aryl-allylaniines were prepared using a palladium-catalysed nucleophilic cleavage reaction.
