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Second-order catalysis by methanol in the epoxide-opening spirocyclization of glycal epoxide 22c (R = H). a) Plot of kobs (min−1) for inversion product formation at varying [CD3OD] yields a polynomial curve. Mean values over two replicate experiments shown. b) Plot of kobs (min−1) versus [CD3OD]2 yields a linear correlation, consistent with second-order dependence on methanol. Mean values over two replicate experiments shown.
