Fig. 5: Synthesis of enamides via transformation of primary amides using 1,1-diborylalkanes.
From: Chemodivergent transformations of amides using gem-diborylalkanes as pro-nucleophiles
Reaction conditions: 1) 1 (0.50 mmol), primiary amide (0.25 mmol), nBuLi (1.0 mmol), THF (2.0 mL), 0 °C, 5 min then 100 °C for 24 h. 2) tBuOH (0.50 mL), 100 °C, 0.5 h then TFAA (1.0 mL), 100 °C, 2 h. Yields based on isolated products. The geometry and ratios of Z/E were determined by NMR analysis and shown in parenthesis. a12 h. TFAA: trifluoroacetic anhydride.
