Table 1. Optimized Reaction Conditions: Standard Deviation Studies.
Entry | Deviation from Standard Reaction Conditiona | Conversion (%) | ee (%) |
---|---|---|---|
1 | None | 95 (81b) | 96 |
2 | 0.5 M instead of 1 M | 60 | 96 |
3 | L2 instead of L1 | 43 | 83 |
4 | L3 instead of L1 | 50 | 92 |
5 | L4 instead of L1 | 70 | 92 |
6 | Cs2CO3 instead of aq. CsOH | 75 | 94 |
7 | No aq. CsOH | 40 | 96 |
8 | Cs2CO3 instead of aq. CsOH; no H2O | <5 | – |
9 | No [Rh(cod)(OH)]2 | <5 | – |
10 | No Ligand | <5 | – |
Reaction conditions: 1 (0.5 mmol, 1 equiv), 2a (1.5 mmol, 3 equiv), [Rh(cod)(OH)]2 (0.015 mmol, 3 mol%), ligand (0.035 mmol, 7 mol%), aq. CsOH (1 mmol, 2 equiv), THP:Tol (1:1, 0.5 mL), H2O (0.25 mL), 70 °C, 20 h.
Isolated yield (%).