Stereoselective synthesis of quaternary benzylic carbons using C2 symmetric imidazolines and tetrahydrofuran as electrophile

Quaternary benzylic centers were stereoeselectively prepared via intermolecular reaction, with the 9-BBN triflate/THF system or methyl iodide as electrophiles. Chemical correlation was used to determine absolute configuration for the newly created stereogenic center, which is also an alternative methodology for the alkylation of imidazolines using methyl iodide as electrophile. Low-temperature nuclear magnetic resonance data indicate the presence of N- and C-metalated compounds, the formation of which may be the stereodeterminant step of the alkylation.