In summary, we have developed protocols for the intramolecular aza-Michael cyclization of sulfamates and sulfamides onto pendant α,β-unsaturated esters, thioesters, amides, and nitriles. Stirring substrate with catalytic quantities of the appropriate base delivers product in good yield and excellent diastereoselectivity. The reactions are operationally simple, can be performed open to air, and are tolerant of a variety of important functional groups. We have demonstrated the utility of this new reaction by applying it as a key step in the preparation of a (-)negamycin derivative. Overall, we expect this technology to find much use for the controlled preparation of 1,3-aminoalcohols in both academic and industrial contexts.