Nucleophilic substitution on 4-hydroxymethylanilines under 'neutral' conditions via aza quinone methide intermediate

Article abstract of DOI:10.1016/S0040-4039(02)01198-X

Substitution reaction of 4-hydroxymethylaniline derivatives with resonance-stabilized carbon nucleophiles and an acid-labile nucleophile, including β-ketoester, 1,3-diketone, α-nitroester, and silylenolether, proceeded efficiently upon heating at 80°C in a neutral solvent system. The reaction was successfully applied to the synthesis of 4-aminophenylalanine.