Table 1.
Optimization of the Reaction Conditionsa
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| entry | Rh loading (mol %) | 2 (equiv) | solvent | time (h) | yield (%) | ee (%) |
| 1 | 5 | 1.5 | THF | 24 | 39 | 73 |
| 2 | 5 | 1.5 | toluene | 24 | 59 | 85 |
| 3 | 5 | 1.5 | toluene | 6 | 47 | 85 |
| 4 | 5 | 3.0 | toluene | 24 | 72 | 73 |
| 5 | 10 | 1.5 | toluene | 24 | 77 | 92 |
a
Reaction conditions: tertiary allylic trichloroacetimidate 1a or 1 (1 equiv), amine 2 (3 equiv), THF (0.2 M). Isolated yield. (B) All amination reactions were conducted at 0.1 M with 1. Isolated yields are reported; the enantiomeric excess (ee) was determined using chiral HPLC.