Nucleophilic Aminomethylation of Aldehydes with α-Amino Alkylsilanes

Article abstract of DOI:10.1246/bcsj.58.1991

Fluoride-induced desilylation of (α-phthalimido-, α-morpholino-, and α-acetamidobenzyl)silanes and a (phthalimidomethyl)silane generates the corresponding α-amino carbanions which add to a variety of aldehydes.The conversion of phthalimido group of the adducts into amino moiety leads to β-amino alcohols.This simple reaction sequence offers a new and general method of nucleophilic aminomethylation.