Table 1. Optimization Studies.
entry | Conditions | 4 yield (%)a | e.e. (%) |
---|---|---|---|
1 | Ligand L1, L2 or L3 | <5 | – |
2 | Ligand L4 | 44 | 20 |
3 | Ligand L5 | 33 | 30 |
4 | Ligand L6 | 72 | 40 |
5 | Ligand L7 | 49 | 64 |
6 | Ligand L8 | 45 | 74 |
7 | Ligand L9 | >95 | 90 |
8 | L9, EtOAc instead of Et2O | 80 | 84 |
9 | L9, MTBE instead of Et2O | 89 | 89 |
10 | L9, Toluene instead of Et2O | 91 | 91 |
11b | L9, 0.40 mmol of 1 | >95 | 94 |
NMR yields.
Reaction performed using 1.25 mol % of Pd2(dba)3·CHCl3 and 3.5 mol % of (S,S)-ligand.