Table 2.
| ||||
---|---|---|---|---|
entry | benzylic alcohol | ee (%) | yield (%)b | |
1 | R =Me | 88 | 88 | |
2 | Et | 94 | 92 | |
3 | n-Pr | 94 | 90 | |
4 | n-Bu | 95 | 83 | |
5 | i-Bu | 95 | 77 | |
6 | cyclobutyl | 94 | 51 | |
7c | 95 | 80 | ||
8 | 88 | 90 | ||
9 | 86 | 59 | ||
10d | 94 | 77 | ||
11 | 92 | 84 | ||
12 | 94 | 84 | ||
13 | 95 | 88 | ||
14 | 94 | 75 | ||
|
||||
15 | X = F | 93 | 87 | |
16 | Cl | 90 | 88 | |
17 | Br | 91 | 79 | |
18 | Ph | 92 | 78 | |
19e | X = OMe | 95 | 94 | |
20c,e | OPiv | 84 | 84 | |
|
||||
21e | X = OMe | 94 | 94 | |
22c | CF3 | 89 | 63 | |
23e | 92 | 88 | ||
|
||||
24 | 81 | 66 | ||
25 | 91 | 79 | ||
26 | 93 | 88 | ||
27 | 83 | 54 | ||
28 | 94 | 93 |
All data are the average of two experiments.
Yield of purified product.
Reaction temperature: −35 °C.
Nucleophile: (p-tolyl)ZnI.
Nucleophile: PhZnI.