132565-55-0Relevant academic research and scientific papers
Carbocyclic Amino Ketones by Bredt's Rule-Arrested Kulinkovich-de Meijere Reaction
Finn, Paul B.,Derstine, Brenden P.,Sieburth, Scott McN.
, p. 2536 - 2539 (2016)
The TiII-mediated formation of cyclopropylamines from alkenes and amides, the Kulinkovich-de Meijere reaction, involves two carbon-carbon bond-forming steps. Strategic use of a tricyclic intermediate can arrest the process if the second step requires formation of a bridgehead double bond. Use of this Bredt's rule constraint results in the production of carbocyclic amino ketones, key alkaloid building blocks. Frustrated by Bredt's rule: An inability to consummate a Kulinkovich-de Meijere cyclopropanation that would involve a bridgehead double bond transforms the reaction into a transannular cyclization of an unsaturated lactam yielding an amino ketone product with potential for alkaloid synthesis.
Synthesis of (+)-kuraramine
Frigerio, Fabio,Haseler, Claire A.,Gallagher, Timothy
supporting information; experimental part, p. 729 - 730 (2010/06/19)
The first synthesis of (+)-kuraramine via oxidative cleavage of (-)-N-methylcytisine is reported. An alternative but unsuccessful approach to (+)-kuraramine is also described based on extending an intramolecular enolate addition protocol that had previous
New Synthesis of Nitrogen Heterocycles through Amide-Directed Hydrocarbonylation of Alkenamides Catalyzed by Rhodium Complexes
Ojima, Iwao,Korda, Anna,Shay, William R.
, p. 2024 - 2030 (2007/10/02)
Amide-directed hydrocarbonylation of 3-butenamide (1) catalyzed by rhodium complexes such as RhCl(PPh3)3, RhCl(CO)(PPh3)2, HRh(CO)(PPh3)3, and Rh4(CO)12 gives a mixture of 3,4-dihydro-2-pyridone (2), 4-methyl-3-pyrrolin-2-one (3), and a unique heterodimer
