Direct regio- and stereo-selective lithiation of secondary allyl and methylallyl amines: reaction with electrophiles

Abstract

Several secondary allyl and methylallyl amines (1) have been regio- and stereo-selectively lithiated with t-butyl-lithium, giving the corresponding sp²γ-aminated organolithium intermediates (2), which by reaction with electrophiles (D₂O, Me₂S₂, PrⁱCHO, PhCHO, Me₂CO, or Ph₂CO) give the products (3) expected from S_E reaction with retention of configuration; in the case of methylallylaniline (1f), the corresponding intermediate (2f) and products (3f) were obtained, under similar reaction conditions.