Table 3.
Phosphine-Catalyzed Asymmetric Synthesis of Benzylic Ethers: Scope with Respect to the Alcohola
| |||
|---|---|---|---|
| entry | H–OR | ee (%) | yield (%)b |
| 1 |
|
95 | 90 |
| 2 | 94 | 88 | |
| 3c | 91 | 86 | |
| 4 |
|
94 | 88 |
| 5 |
|
91 | 86 |
| 6c |
|
93 | 74 |
| 7d | HOMe | 92 | 88 |
| 8 |
|
96 | 82 |
| 9 |
|
96 (95e) | 64 (79e) |
| 10 |
|
96 | 75 |
All data are the average of two experiments.
Yield of purified, isolated product.
Amount of nucleophile: 2.0 equiv.
The methyl, rather than the t-butyl, ester of the alkynoate was used.
Catalyst loading: 20% (S)–1.