Selective synthesis of seven- and eight-membered ring sultams via two tandem reaction protocols from one starting material.

Abstract

From one starting material, two tandem reaction protocols to synthesize seven- and eight-membered ring sultams were developed. One protocol employs intermolecular epoxide ring-opening by NaN3, followed by an intramolecular 7-endo-trig oxa-Michael addition reaction. The second protocol applies to intermolecular aza-Michael addition of a primary amine, followed by 8-endo-tet intramolecular epoxide ring-opening of the resultant amine intermediate. Both protocols afforded the respective sultams in good yields under mild reaction conditions.

DOI: 10.1021/ol301535j

Cite this paper

@article{Wang2012SelectiveSO, title={Selective synthesis of seven- and eight-membered ring sultams via two tandem reaction protocols from one starting material.}, author={Min Wang and Yanjie Wang and Xueyong Qi and Guohua Xia and Kun Tong and Jinchang Tu and C. U. Pittman and Aihua Zhou}, journal={Organic letters}, year={2012}, volume={14 14}, pages={3700-3} }