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. 2015 Jan 16;137(3):1330–1340. doi: 10.1021/ja512022r

Scheme 11. Successful Installation of the Butenolide Moiety via a Hydrazone–Boronic Acid Coupling Strategy.

Scheme 11

Reagents and conditions: (a) [Ir(OMe)(cod)]2 (0.05 equiv), dtbpy (0.1 equiv), 2-norbornene (1.5 equiv), PhMe2SiH (1.5 equiv), 80 °C, 8 h, 43%; (b) NaIO4 (3 equiv), HCl (1 M, 0.7 equiv), 4:1 THF:H2O, 23 °C, 2 h, 91%; (c) TsNHNH2 (1.5 equiv), dioxane, 110 °C, 5 h, 64%; (d) K2CO3 (2.2 equiv), dioxane, 110 °C, 5 h, ca. 20%; (e) AcOOH (32 wt % in H2O), NaOAc (5 equiv), CH2Cl2, 23 °C, 24 h, ca. 70%.