Table 2.
entry | substrate | product | time (h) | yield (%)a | ee (%)b |
---|---|---|---|---|---|
1c,d |
5c |
6 |
48 | 74 | 91 |
2 |
11 R=Me R′=H |
12 | 72 | 70 | 90 |
3 |
13 R=H R′=Me |
14 | 72 | 66 | 89 |
4 |
15 R=Me R′=Me |
16 | 96 | 51 | 89 |
5 |
17 R=H R′=Ph |
18 | 72 | 48 | 86 |
6 |
19 R=CO2Et R′=H |
20 | 72 | 66 | 90 |
7e |
21 R=CO2Me R′=Me |
22 | 96 | 37 | 80 |
8c,d |
23 |
24 |
72 | 54 | 95 |
9 |
25 |
26 |
72 | 42 | 88 |
10d |
27 |
28 |
72 | 77 | 90 |
11 |
29 |
30 |
72 | 70f | 89f |
Isolated yields after chromatography on silica gel.
Determined by HPLC using commercial chiral columns.
10 mol% 10 + 8.
The absolute stereochemistry of 24 and derivatives of 28 and 6 were determined by Xray crystallography and that of all other products was assigned by analogy.
20 mol% 10 + 8.
Determined on the free alcohol.