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. 2015 Jun 12;6(8):4973–4977. doi: 10.1039/c5sc01589h

Table 2. The role of the base a .

Inline graphic
Entry Base (equiv.) 11 (equiv.) 12 b (%) Notes
1 KHMDS (2.0) 2.0 81
2 NaHMDS (2.0) 0.10 80
3 KOtBu (2.0) 0.10 60 Side-products observed
4 KHMDS (0.5) Only 1a and 1d observed
5 NaHMDS (0.5) 24 Side-products observed
6 c KHMDS (0.5) Only 1a and 1d observed

aConditions: benzyl chloride (0.24 mmol, 1.2 equiv., or none), imine 1a (0.2 mmol, 1.0 equiv.), base (0.4 mmol or 0.1 mmol, 2.0 equiv. or 0.5 equiv.), toluene (0.6 mmol), 45 °C, 3 hours.

bCalculated by NMR analysis using dimethyl malonate as an internal standard.

cReaction performed in the presence of 5% [Ni(COD)2]/10% IPr.