Lewis Base-Bronsted Acid Co-catalyzed Morita-Baylis-Hillman Reaction of Cyclic Sulfamidate Imines

A Lewis base-Bronsted acid co-catalyzed Morita-Baylis-Hillman reaction of cyclic sulfamidate imines with acrylate-type Michael acceptors has been developed. The combination of equimolecular catalytic amounts of DABCO and acetic acid proved highly efficient and tolerated well a wide range of Michael acceptors and substituted 6-membered ring sulfamidate imines, as well as a sultam derivative. The reaction provides a straightforward access to sulfamidates bearing alpha,beta-unsaturated chains, which allows for the further functionalization of the products. Moreover, the robustness and applicability of the method was demonstrated by performing a gram scale reaction and further functionalization of the MBH-adducts.

Automated summary

The Lewis base-Brønsted acid co-catalyzed Morita-Baylis-Hillman reaction of cyclic sulfamidate imines with acrylate-type Michael acceptors using equimolecular amounts of DABCO and acetic acid proved highly efficient and tolerated a wide range of substrates. The reaction provides a straightforward access to sulfamidates bearing alpha,beta-unsaturated chains, allowing for further functionalization of the products. The robustness and applicability of the method was demonstrated by performing a gram scale reaction and further functionalization of the MBH-adducts.