Provide a reasonable mechanism to account for the formation of compound 2, including a

Chapter 22, Problem 22.119

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Provide a reasonable mechanism to account for the formation of compound 2, including a rationale to explain the observed stereochemistry of the product (Org. Lett. 2012, 14, 47384741). Note that NaHMDS is a strong base, comparable to LDA. (Hint: Consider both resonance structures of the intermediate formed in the first step of the mechanism.) O O Na (NaHMDS) O OH 1) 2) H2O 1 2 N TMS TMS ! @

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