An efficient method to convert lactams and amides into 2,2-dialkylated amines.
A practical method for the synthesis of gem-2,2-disubstituted tertiary amines from the corresponding lactams (or amides) is reported. It is based on the reaction of thioiminium ions, easily prepared from lactams and amides with organometallic reagents such allylmagnesium, benzylmagnesium, and primary alkylcerium reagents.
Agosti
Alessandro
A
Universität Bern, Departement für Chemie und Biochemie, Freiestrasse 3, 3012-Bern, Switzerland.
Britto
Sebastian
S
Renaud
Philippe
P
D000577:Amides / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007202:Indicators and Reagents; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; D007202:Indicators and Reagents; D007769:Lactams