Table 5.
entry | substrate | producta | yield,b % | e.r.d |
---|---|---|---|---|
1. |
(E)-29 |
28f |
97% | 68.9:31.1 |
2. |
(E)-30 |
31 |
86% | 74.9:25.1 |
3. |
(E)-36 |
37 |
94% 37:38 = 1.4:1c |
78.8:21.2 |
38 |
85.1:14.9 | |||
4. |
(E)-39 |
40 |
86% 40:41 = 4.5:1c |
82.6:17.4 |
41 |
83.8:16.2 | |||
5. |
(Z)-29 |
42 |
80% | 50.9:49.1 |
Aryl = 2-nitrophenyl.
Reaction conditions: alkene (1.0 mmol), 34 (1.1 mmol), MsOH (1.0 equiv), 35m (0.1 mmol), CHCl3 (0.1 M), 25 °C.
Exo:Endo ratios determined by 1H NMR spectroscopic analysis of the crude reaction mixture.
Determined by CSP-SFC analysis