600153-17-1Relevant articles and documents
Unusual skeletal rearrangement of unsaturated seven-membered lactams into fused pyrrolidinolactones
Alvarez, Silvia,Dominguez, Gema,Gradillas, Ana,Perez-Castells, Javier
, p. 3094 - 3102 (2013)
Unsaturated ε-lactams undergo a novel process involving a skeletal reorganization to give fused pyrrolidine-lactones by reaction with aromatic α-bromo ketones in the presence of 1,4-diazabicyclo[2.2.2]octane and a base. The process involves the formation
Bronsted base-modulated Regioselective Pd-catalyzed intramolecular aerobic oxidative amination of alkenes: Formation of seven-membered amides and evidence for allylic C-H activation
Wu, Liang,Qiu, Shuifa,Liu, Guosheng
supporting information; experimental part, p. 2707 - 2710 (2009/10/10)
A novel palladium-catalyzed intramolecular aerobic oxidative allylic C-H amination of olefins has been developed. Bronsted base can modulate the regioselectivity, favoring the formation of 7-membered rings. Mechanistic studies using deuterium-labeled substrates as probes support a rate-determining allylic C-H activation/irreversible reductive elimination pathway.
Novel synthetic approach to nine-membered diallylic amides: Stereochemical behavior and utility as chiral building block
Tomooka, Katsuhiko,Suzuki, Masaki,Uehara, Kazuhiro,Shimada, Maki,Akiyama, Toshiyuki
scheme or table, p. 2518 - 2522 (2009/04/10)
An efficient approach to nine-membered diallylic cyclic amides having a variety of substituents has been developed. The synthesized amides have stable planar chirality at ambient temperature. The transformation of the enantiomerically enriched amides provides optically active compounds containing stereogenic centers in a stereospecific fashion. As a demonstration of the synthetic utility of the amides, we have synthesized (+)-γ-lycorane using such an optically active amide as a chiral building block. Georg Thieme Verlag Stuttgart.
