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A Facile Route to Polysubstituted N-Benzyl Pyroglutamates

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posted on 10.04.2003 by Pei-Pei Sun, Meng-Yang Chang, Michael Y. Chiang, Nein-Chen Chang
Base-induced coupling/cyclization reactions of α-sulfonylacetamide with various ethyl (Z)-2-bromo-2-propenoates have been carried out. The polysubstituted pyroglutamate carbon skeleton, with three contiguous asymmetric centers, was built up in one step. A ring-closure mechanism is proposed for the reactions.