Synthesis of 1,4-aminoalcohols from substituted dienes and anilines via molybdooxaziridine catalysis

Abstract

Herein we report the MoODipic(HMPA)ONAr promoted 1,4-aminohydroxylation of dienes using anilines as the quantitative source of N. The transformation involves the formation of the active catalyst Ar–N-molybdooxaziridine 1a, the formation of Ar–NO, a hetero-Diels–Alder reaction, and then reductive cleavage to obtain 1,4-aminoalcohols. Initial kinetic and mechanistic data indicate that Ar–NO formation is the rate-determining step and provides evidence for the proposed catalytic cycle.