188302-42-3Relevant articles and documents
Iridium-Catalyzed Reductive Alkylations of Secondary Amides
Ou, Wei,Han, Feng,Hu, Xiu-Ning,Chen, Hang,Huang, Pei-Qiang
supporting information, p. 11354 - 11358 (2018/08/28)
Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.
Synthesis of azetidine and pyrrolidine derivatives through selenium-induced cyclization of secondary homoallylamines - A 77Se NMR study
Pannecoucke, Xavier,Outurquin, Francis,Paulmier, Claude
, p. 995 - 1006 (2007/10/03)
Treatment of α-alkyl and α,α-dialkyl homoallylic amines 1 with PhSeX (X = C1, Br, I), in CH3CN containing sodium carbonate produced mixtures of azetidines 2 and pyrrolidines 3. The cyclization also occurred in the absence of Na2CO3, and the corresponding azetidinium and pyrrolidinium salts 2(HX) and 3(HX) were formed in CDCl3 or CH3CN. The crude reaction mixtures were analysed by 77Se NMR. Each product - 2, 3, 2(HX), and 3(HX) - was characterized by its 77Se chemical shift, and the product ratios were determined for each reaction. The ratios of azetidine 2 to pyrrolidine 3 increased not only according to the steric hindrance around the α-carbon, but also with the nature of the counterion X- (PhSeCl 1, R2 ≠H), produced only the azetidinium salts 2(HI), allowing the isolation of the corresponding azetidines 2, albeit in poor yield. Some reactions were monitored by 77Se NMR at the beginning of the addition-cyclization process. No intermediates were observed when PhSeI was used, but the thermodynamic addition products 5(Br), 5(HBr), and some dibromoselenuranes 8 were detected. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines
Berthe, Benedicte,Outurquin, Francis,Paulmierz.ast, Claude
, p. 1393 - 1396 (2007/10/03)
Homoallyl benzylamines prepared by allylation of the corresponding N-benzylimines, have been subjected to a selenium-induced cyclization under various conditions. At room temperature. the 4-exo and the 5-endo modes are competitive. In acetonitrile, the azetidine has been isolated as the major cyclization product, especially for homoallylamines derived from ketimines. With an excess or selenium reagent, 3-halopyrrolidines have been obtained.
