Regioselective functionalization of bis(trimethylsilyl)methylimines with electrophiles

A very good control of the regioselectivity occurs in the deprotonation of imino derivs. of bis(trimethylsilyl) methylamine (BSMA) followed by quenching with electrophiles. Functionalization at C-1, C-3 or C-4 takes place selectively depending on the nature of the electrophile and of the base employed. This methodol. provides an entry to a wide class of novel, functionalized, silylated imino derivs. Thus, reaction of (Me3Si)2CHNH2 with PhCHO in C6H6 contg. 4A° mol. sieves gave (Me3Si)2CHN:CHPh which on lithiation with MeLi in THF followed by treatment with EtI electrophile gave 55% PhCH:NCMe(SiMe3)2.