4393-07-1Relevant academic research and scientific papers
Electro-Mechanochemical Atom Transfer Radical Cyclizations using Piezoelectric BaTiO3
Bolm, Carsten,Hernández, José G.,Schumacher, Christian
supporting information, p. 16357 - 16360 (2020/07/13)
The formation and regeneration of active CuI species is a fundamental mechanistic step in copper-catalyzed atom transfer radical cyclizations (ATRC). Typically, the presence of the catalytically active CuI species in the reaction mix
Enantio- and diastereoselective syntheses of 3-hydroxypiperidines through iridium-catalyzed allylic substitution
Hoecker, Johannes,Rudolf, Georg C.,Baechle, Florian,Fleischer, Steffen,Lindner, Benjamin D.,Helmchen, Guenter
supporting information, p. 5149 - 5159 (2013/11/06)
Stereoselective syntheses of 3-hydroxypiperidines have been developed. Key intermediates are N-protected allylamines that are prepared by an enantioselective iridium-catalyzed allylic amination. A subsequent catch and release procedure that involves an epoxidation and base-mediated elimination yields δ-lactams that are suitably functionalized to prepare biologically active 3-hydroxypiperidines. In addition, applications of this method to the total syntheses of deoxymannojirimycin, D-erythro-sphingosine, and chiral building blocks of interest for medicinal chemistry are described. Stereoselective syntheses of 3-hydroxypiperidines are reported. The key reactions are an iridium-catalyzed allylic amination and a catch and release procedure that consists of a highly diastereoselective epoxidation and a base-mediated ring opening of the epoxide. This method was applied to the total syntheses of sphingosine, deoxymannojirimycin, and pharmaceutically relevant small molecules. Copyright
A new route to 7-substituted derivatives of N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl) -ethyl]benzoyl}-L-glutamic acid [ALIMTA (LY231514, MTA)]
Taylor,Liu
, p. 3726 - 3738 (2007/10/03)
Alkylation of various primary amines with crotyl bromide, followed by DMAP-promoted acylation with methyl malonyl chloride to 4 and then manganic triacetate dihydrate/cupric acetate induced radical cyclization, gave 1-substituted-4-vinyl-3-carbomethoxy-2-pyrrolidinones (5). Thiation to the thiolactams 6 and guanidine cyclization then gave a series of 2-amino-3,4-dihydro-4-oxo-5-vinyl-7-substituted pyrrolo[2,3-d]pyrimidines (7). Palladium-catalyzed C-C coupling with diethyl 4-iodobenzoylglutamate led in one step via an unexpected redox reaction to the diethyl esters 9 of a series of 7-substituted derivatives of ALIMTA (LY231514, MTA), from which the target analogues 10 were readily prepared by saponification. Attempted deprotection at position 7 was successful in only one case (9d, R = CH2C6H3(OMe)2 (-3′,4′), which resulted in a known pentultimate precursor (9, R = H) of ALIMTA. The 7-substituted derivatives 10 proved to be inactive in vitro as inhibitors of cell division.
PHOSPHONIUM DIAZA-DIYLIDS AND AZA-YLDIID AS NEW AND EFFICIENT REAGENTS FOR PRIMARY AND SECONDARY AMINES SYNTHESIS
Cristau, Henri-Jean,Garcia, Chantal,Kadoura, Jumah,Torreilles, Eliane
, p. 151 - 154 (2007/10/02)
Metallated aminophosphonium ylids, diaza-diylids and aza-yldiid, are investigated as reagents for primary and secondary amines synthesis.
Contribution a l'evaluation de l'importance des facteurs electroniques et steriques gouvernant la reaction des boranes avec les azides
Carboni, Bertrand,Vaultier, Michel,Courgeon, Thierry,Carrie, Robert
, p. 844 - 849 (2007/10/02)
Organoboranes react with azides to give, after hydrolysis, secondary amines.Scope and limitations of this method have been stated.When dibromoboranes were used, a competitive migration of the alkyl group and bromine leading to the simultaneous formation of a tetraazaboroline and the expected secondary amine was observed.A mechanism accounting for these results is proposed.
