Organic Letters p. 3700 - 3703 (2012)
Update date:2022-08-04
Topics:
Wang, Min
Wang, Yanjie
Qi, Xueyong
Xia, Guohua
Tong, Kun
Tu, Jinchang
Pittman, Charles U.
Zhou, Aihua
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.
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(2013)