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 SE reaction with retention of configuration; in the case of methylallylaniline (1f), the corresponding intermediate (2f) and products (3f) were obtained, under similar reaction conditions.
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Barluenga et al. (1988) studied this question.