Discodermolide C1-C7 fragment: spot the stereochemistry flaw

Single question

Evans syn-aldol on a propionate auxiliary, then auxiliary cleavage to give the C1-C7 acid. Reagents and reaction class are right. Look hard at the relative configuration of the new methyl and the new hydroxyl.

Evans syn-aldol stereochemistry

Distinguishing syn-propionate from anti-propionate

Auxiliary chirality dictates the new C-C bond face

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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