Journal of Organic Chemistry p. 7549 - 7557 (2020)
Update date:2022-08-03
Topics:
Duddupudi, Anantha Lakshmi
Pandey, Pankaj
Vo, Hien
Welsh, Colin L.
Doerksen, Robert J.
Cuny, Gregory D.
A metal-free oxidative cyclization of N-Boc-acrylamides with (diacetoxyiodo)benzene in acetic acid produced 5,5-disubstituted oxazolidine-2,4-diones with the formation of a C-O bond in moderate to excellent yields. In addition, the reaction was diastereospecific with N-Boc-2,3-dimethylacrylamides and proceeded with phenyl migration in the case of an N-Boc-2-phenylacrylamide to generate a 5-acetoxy-5-benzyloxazolidine-2,4-dione.
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