Intramolecular nucleophilic catalysis and the exceptional reactivity of N-benzyloxycarbonyl α-aminophosphonochloridates

Abstract

The chloridate BnOCONHCH₂P(O)(OMe)Cl is 10³–10⁴ times more reactive than ClCH₂P(O)(OMe)Cl in substitution with PrⁱOH; the α,α-dimethyl analogue is no less reactive and the N-methyl derivative is more reactive; nucleophilic participation (catalysis) by the carbamate group is implicated.