Compound 2 was used as a key intermediate in a synthesis

Chapter 11, Problem 11.57

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Compound 2 was used as a key intermediate in a synthesis of oseltamivir, an anti-influenza agent (J. Am. Chem. Soc. 2006; 128, 63106311). Propose a plausible mechanism for the conversion of 1 to 2, as shown, and explain the stereochemical outcome: N O R I N O R Br 1 2 1) t-BuOK 2) NBS, h

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