Table 2.
| ||||
---|---|---|---|---|
entry | electrophile | product | yield (%) |
er (R:S) |
1a | 63 | 92:8 | ||
2a,b | 59 | 6:94 | ||
3a | 75 | 97:3 | ||
4a | 69 | 95:5 | ||
5a | 64 | 92:8 | ||
6a | 60 | 91:9 | ||
7a,c | 66 | 90:10 | ||
8a | 60 | 93:7 | ||
9e | 67 | 97:3 | ||
10d | 46 | 88:12 | ||
11b,d | 51 | 10:90 | ||
12d | 50 | 93:7 | ||
13d | 53 | 85:15 | ||
14a | 63 | 92:8 | ||
15a,e | 66 | 93:7 |
stirred at rt for 18 h during step (iv),
CDR using (S,R)-2;
the aryl bromide contained a small amount of 2-bromobenzonitrile leading to formation of the ortho cyano constitutional isomer in 90:10 er;
stirred at 60 °C for 22 h during step (iv),
a small amount of the Z-alkene was obtained as a minor isomer in 92:8 er.