64871-53-0Relevant academic research and scientific papers
Enantioselective synthesis of N-heterocycles via intramolecular Pd(0)-catalysed allylic amination
Olszewska, Beata,Kryczka, Bogus?aw,Zawisza, Anna
, p. 9551 - 9556 (2013/10/22)
An efficient and stereoselective synthesis of pyrrolidine-, piperidine-, and azepane-type N-heterocycles is described by the intramolecular Pd(0)-catalysed cyclisation of amino allylic carbonates. The use of chiral ligands gave the corresponding heterocyclic derivatives having er values that were from moderate to good.
Organolithium or Heck-type cyclization of N-ortho-iodobenzyl-2- alkenylpyrrolidines to give indolizidines
García-Calvo, Oihane,Sotomayor, Nuria,Lete, Esther,Coldham, Iain
, p. 57 - 66 (2011/06/25)
Carbolithiation reactions of 2-alkenyl-substituted pyrrolidines have been studied. An electron-withdrawing group in the alkene (R = CONEt2) is required for the 6-exo-trig cyclization to afford hexahydropyrrolo[1,2-b]isoquinolines. Alternatively, the cyclization of the unactivated alkene can be performed under Heck conditions. ARKAT USA, Inc.
Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information; experimental part, p. 1334 - 1337 (2011/05/15)
A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF 6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.
Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines
Tsuhako, Akiko,Oikawa, Daisuke,Sakai, Kazushi,Okamoto, Sentaro
scheme or table, p. 6529 - 6532 (2009/04/06)
Copper salts, such as CuCl, CuI, CuCl2 and Cu(OTf)2, were used to catalyze the intramolecular hydroamination of allenylamines to provide the corresponding 3-pyrrolines or 2-alkenylpyrrolidines.
Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement
Bremner, John B.,Perkins, David F.
, p. 2659 - 2665 (2007/10/03)
This paper describes the synthesis of functionalised azecine and azonine derivatives incorporating the adrenaline motif. In a key step, an enolate assisted aza Claisen rearrangement was employed to interconvert from 6- and 5-membered heterocycles to their corresponding 10- and 9-membered lactams.
Palladium-catalyzed reactions of N-allylbenzotriazoles with amines: Intramolecular allylamination routes to 2-vinylpyrrolidines and 2- vinylpiperidines
Katritzky, Alan R.,Yao, Jiangchao,Yang, Baozhen
, p. 6066 - 6070 (2007/10/03)
Reactions of allylbenzotriazole (4a-d) with 1-bromo-3-chloropropane, 1- bromo-2-methyl-3-chloropropane, epibromohydrin (8), and 1-bromo-4- chlorobutane afforded the corresponding α-substituted allylbenzotriazoles (5a-d, 9, and 16a,b), which with primary amines in one-pot sequences produce 2-vinylpyrrolidines (7a-i), 2-ethylpyrrole (13), and 2-vinylpiperidines (18a- c) in good yields under mild conditions.
A new method for the synthesis of nitrogen heterocycles via palladium catalyzed intramolecular hydroamination of allenes
Meguro, Masaki,Yamamoto, Yoshinori
, p. 5421 - 5424 (2007/10/03)
The intramolecular hydroamination of certain allenes, beating amine or sulfonyl amide groups at the terminus of the carbon chain, proceeded smoothly in the presence of catalytic amounts of palladium complex ([(η3- C3H5)PdC
CYCLISATION D'AMINES γ ET δ-ALLENIQUES. SYNTHESE D'ALCENYL-2 PYRROLIDINES ET D'ALCENYL-2- PIPERIDINES
Arseniyadis, Simeon,Gore, Jacques
, p. 3997 - 4000 (2007/10/02)
The entitled heterocyclic compounds can be obtained with good yields and exclusively with E configuration by the respective cyclisation of secondary γ-allenic and δ-allenic amines promoted by silver nitrate or by mercuric chloride.In the second case, the
