Table 1.
Entry | E+ | Product(s) | % Yield | er |
---|---|---|---|---|
1 | Me3SiCl | (S)-3 | 74 | 96:4 |
2 | Bu3SnCl | (S)-10 | 66 | 96:4 |
3 | Bu3SnCl | (R)-10 | 62 | 97:3a |
4 | CO2 | (R)-11 | 78 | 98:2 |
5 | MeOCOCl | (R)-12 | 88 | >99:1 |
6 | MeOCOCl | (S)-12 | 85 | >99:1a |
7 | PhNCO | (R)-13 | 68 | >99:1 |
8 | Allyl bromide | (R)-14 | 63 | 95:5b |
9 | Allyl bromide | (S)-14 | 59 | 96:4a,b |
10 | BnBr | (R)-15 | 65 | >99:1b |
11 | Cyclohexanone |
(R)-16 |
60 | 94:6 |
12 | PhCHOc |
17 |
74 (62:38 dr) | >99:1 & 98:2 |
13 | 1-NpCHOc |
18 |
66 (82:18 dr) | 94:6 & 93:7 |
14 | CH3CHOc |
19 |
78 (85:15 dr) | >99:1 for both |
Using ligand 9
via Negishi cross coupling
Major diastereomer illustrated