Virginie Pevere

Straightforward synthesis of N-protected benzylic amines by carbamoalkylation of aromatic compounds

Abstract A wide range of alkoxycarbonyl protected benzylic amines have been synthesized in a three component reaction involving a carbamate an aldehyde and an aromatic substrate. This reaction proceeds through electrophilic substitution of the aromatic compound by a N-carbamoyl iminium which is generated in situ by condensation of the carbamate with the aldehyde.

Mesyl guaiacol: a versatile intermediate for the synthesis of 5-aminomethyl guaiacol and related compounds

Abstract An original synthetic pathway for the preparation of 5-substituted guaiacol derivatives is described. This method relies on the deactivation of the phenol group by converting it into the corresponding mesyl ester. Amidomethylation reactions lead to regioselective CC bond formation at the 5-position of guaiacol. Thus, 5-aminomethyl-guaiacol was obtained in four steps and 75% overall yield.

Directed ortho-Metalation, a New Insight into Organosodium Chemistry

alkylsodium com-pounds have not been considered so far as valuable organo-metallic reagents in organic synthesis.Herein we report on a straightforward and efficient one-potortho-metalation procedure relying on the generation ofsodiated organic bases from RCl and a stoichiometric amountof metallic sodium in the presence of aromatic substrates.