Table 2. Results of studies utilizing (1S,2R)-aminoindanol 24 with aldehyde 6.
| Entry | Isocyanide (equiv.) | Temp. (°C) | Yielda,b (%) | drc (a : b) |
|---|---|---|---|---|
| 1 | 1 | 0 °C to 23 °C | 17 | 89 : 11 |
| 2 | 1.5 | 0 °C to 23 °C | 25 | 90 : 10 |
| 3 | 2 | 0 °C to 23 °C | 23 | 88 : 12 |
| 4 | 3 | 0 °C to 23 °C | 30 | 87 : 13 |
| 5 | 2 | 0 °C to 40 °C | 37 | 91 : 9 |
| 6 | 2 | 0 °C to 50 °C | 27 | 85 : 15 |
| 7 | 2 | 0 °C to 60 °C | 28 | 80 : 20 |
a
All reactions are done in 0.2 M MeOH relative to aldehyde. Aldehyde (2 equiv.), acid (1 equiv.), amine (1 equiv.) were used at specified temperature for 24 h.
b
Isolated yield after chromatography.
c
The dr obtained via HPLC analysis of mixture after chromatography.