Table 5.
Scope of Aldehyde Moiety at room temperature.a
| Entry | R | Time (h) | Yield (Product) | eeb | drc |
|---|---|---|---|---|---|
| 1 | pentafluorophenyl- | 13 | 97 (17) | >99 | >99:1 |
| 2 | 2,4-dinitrophenyl- | 40 | 99 (17) | 96 | 57:1 |
| 3 | 2,6-dichlorophenyl- | 48 | 99 (17) | 99 | >99:1 |
| 4 | 4-pyridyl- | 12 | 92 (17) | 99 | 50:1 |
| 5 | 2-naphthyl- | 48 | 63 (17k) | >99 | >99:1 |
| 6 | phenylethyl- | 72 | 32 (17l) | 59 | 29:1 |
a
All reactions were performed at 2 M concentration of 16 in solution and with five equivalents of 5.
b
Determined by chiral HPLC analysis.
c
Determined by 1H NMR analysis.