Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the .alpha.-position of amines utilizing anodic oxidation as a key step

Recent Developments in the ^|^ldquo;Cation Pool^|^rdquo; Method

“…10 Low temperature electrochemical oxidation of a carbamate gives a pool of the corresponding N acyliminium ion, which can be characterized by NMR and IR. The resulting N acyliminium ion pool reacts with various nucleophiles as shown in Scheme 4.…”

Anodic Alkoxylation of Lactams Followed by Reactions with Carbon Nucleophiles in a One-Pot Manner Using HFIP as a Solvent

“…The reaction mixture was added to water (15 mL) and extracted repeatedly with CH 2 Cl 2 (3 © 30 mL). The combined extracts were neutralized with saturated aqueous NaHCO 3 , washed with brine, and dried over anhydrous Na 2 SO 4 . After removal of the drying agent, the organic layer was concentrated under reduced pressure and the residue was purified over silica gel column to obtain the allylated product, which was identified by comparison with literature values (3a 15 and 3b …”

“…2 Shono and co-workers demonstrated anodic methoxylation of carbamates and subsequent C-C bond forming reactions under Lewis acid conditions as shown in Scheme 1. 3,4 However, it requires replacement of the solvent after the electrolysis. In order to overcome the problem, direct oxidative C-C bond forming reactions have been developed to date.…”

Synthesis via N-acyliminium cyclisations of N-heterocyclic ring systems related to alkaloids

“…Tropane-like systems can be prepared by Lewis acid-induced cyclisation of alkene 44 or enolic 45 π-nucleophiles (Scheme 29).…”