3378-71-0Relevant articles and documents
An improved reduction procedure in the synthesis of substituted pyrrolidines via an aminomercuration/reduction sequence of primary alkenylamines
Roubaud, Valerie,Le Moigne, Francois,Mercier, Anne,Tordo, Paul
, p. 1507 - 1516 (1996)
Aminomercuration/reduction sequence of δ-alkenylamines is a typical route to substituted pyrrolidines. Backward reaction to the starting material is a major drawback which occurs during sodium borohydride reduction of the intermediate organomercurial. We describe here a new reduction procedure which prevents almost completely this backward reaction and leads to significant increases in the yields of pyrrolidines.
Reactivity of functionalized indoles with rare-earth metal amides. Synthesis, characterization and catalytic activity of rare-earth metal complexes incorporating indolyl ligands
Feng, Zhijun,Wei, Yun,Zhou, Shuangliu,Zhang, Guangchao,Zhu, Xiancui,Guo, Liping,Wang, Shaowu,Mu, Xiaolong
, p. 20502 - 20513 (2015/12/05)
The reactivity of several functionalized indoles 2-(RNHCH2)C8H5NH (R = C6H5 (1), tBu (2), 2,6-iPr2C6H3 (3)) with rare-earth metal amides is described. Reactions of 1 or 2 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Eu, Yb) respectively produced the europium complexes [2-(C6H5NCH)C8H5N]2Eu[N(SiMe3)2] (4) and [2-(tBuNCH)C8H5N]Eu[N(SiMe3)2]2 (5), and the ytterbium complex [2-(tBuNCH)C8H5N]2Yb[N(SiMe3)2] (6), containing bidentate anionic indolyl ligands via dehydrogenation of the amine to the imine. In contrast, reactions of the more sterically bulky indole 3 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 afforded complexes [2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2](THF)2 (RE = Yb (7), Y (8), Er (9), Dy (10)) with the deprotonated indolyl ligand. While reactions of 3 with yttrium and ytterbium amides in refluxing toluene respectively gave the complexes [2-(2,6-iPr2C6H3NCH)C8H5N]3Y (11) and [2-(2,6-iPr2C6H3NCH)C8H5N]2YbII(THF)2 (12), along with transformation of the amino group to the imino group, and also with a reduction of Yb3+ to Yb2+ in the formation of 12. Reactions of 3 with samarium and neodymium amides provided novel dinuclear complexes {[μ-η5:η1:η1-2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2]}2 (RE = Sm (13), Nd (14)) having indolyl ligands in μ-η5:η1:η1 hapticities. The pathway for the transformation of the amino group to the imino group is proposed on the basis of the experimental results. The new complexes displayed excellent activity in the intramolecular hydroamination of aminoalkenes.
Highly active and diastereoselective N,O- and N,N-yttrium complexes for intramolecular hydroamination
Lauterwasser, Frank,Hayes, Paul G.,Piers, Warren E.,Schafer, Laurel L.,Braese, Stefan
experimental part, p. 1384 - 1390 (2011/06/26)
The intramolecular hydroamination of aminoalkynes and unactivated aminoalkenes catalyzed by yttrium N,O- and N,N-complexes has been investigated. The N,N-yttrium complexes are highly active, catalyzing the conversion of a wide range of terminal aminoalkenes at room temperature, and internal aminoalkenes at elevated temperature, to yield pyrrolidine and piperidine products in high yields. A high diastereoselectivity of up to 23:1 is observed at 0°C with 1-methyl-4-pentenylamine as substrate.
