Table 3.
Reduction of representative chiral ketones using 1%mol of aminoborate ester 1.a
| Entry | Substrate | Yield (%)b | Ee (%)c | Config.d14 |
|---|---|---|---|---|
| 1e |
|
93 | 95 | (R) |
| 2 |
|
91 | 96 | (R) |
| 3 |
|
90 | 96 | (R) |
| 4 |
|
92 | 99 | (R) |
| 5 |
|
95 | 99 | (R) |
| 6 |
|
88 | 98 | (S) |
| 7 |
|
94 | 99 | (R) |
The reduction was carried out using 0.7 equivalent of borane-DMS in THF at room temperature.
Isolated yield after distillation in a Kugelrohr apparatus.
Determined by GC of acetate on chiral column.
Absolute configuration was determined by comparison of optical rotations with literature values. The configuration of new optical active compounds was assigned by analogy.
The reduction was carried out using 1.7 equivalent of borane-DMS.