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Asymmetric TMM cycloaddition to generate precursors to spirocyclic oxindole natural products.
 | |||||||
|---|---|---|---|---|---|---|---|
| entry | Substrate | Ligand | T, °C | Yield (%) | dr (50:51) | 50, %ee | 51, %ee |
| 1 |  |
L14 | −20 | 96 | 1.3:1 | >99 | 99 |
| 2 | L13 | 0 | 97 | 14:1 | 96 | 80 | |
| 3 |  |
L14 | −20 | 99 | 1:2.3 | 99 | >99 |
| 4 | L13 | 0 | 99 | 15:1 | 86 | 76 | |
All reactions were performed at 0.2 M in toluene with 1.5 equivalents 45, 2.5 mol% Pd2(dba)3•CHCl3 and 10 mol% ligand for 12 hours. Yields were combined, isolated product; ee’s were determined by chiral HPLC.
