Synthesis of aminoalcohols from substituted alkenes via tungstenooxaziridine catalysis†
Abstract
Herein we report the WO2Dipic(H2O) promoted oxyamination of alkenes using sulfonamides as the quantitative source of N. The reaction works for activated and unactivated alkenes in high yields, diastereoselectivities, and stereospecificity. A catalytic cycle involving the formation of tungstenooxaziridine complex 1 as the active catalyst and hydrolysis of tungstenooxazolidine intermediate A as the rate-determining-step has been proposed. Initial kinetic and competition experiments provide evidence for the proposed mechanism.