Table 1. Photochemical [2 + 2] cycloadditions of diesters 6 and synthesis of cyclobutane diesters 7.
| |||||
|---|---|---|---|---|---|
| Entry | Cycloaddition product | Yield of 15 (%)a | Final product | Yield of 7 (%)a | |
| Powder | solutionb | ||||
| 1 |
|
88 | 88 (dr = 97 : 3)c |
|
75 |
| 2 |
|
11 | 64 (dr = 93 : 7)c |
|
91 |
| 3 |
|
35 | 85 (dr = 96 : 4)c |
|
87 |
Yields refer to isolated product yields after purification by column chromatography.
Photochemical solution reactions were conducted in CHCl3 in quartz test tubes.
Diastereomeric ratio (dr) values of the crude reaction mixtures were determined by 1H NMR spectroscopy. The products were obtained as single diastereomers after purification.