Table 3.
[3+2] Cycloaddition ofstyrene (2a) with bicyclic cyclopropylamines 5.[a]
Entry | Substrate | Product[b] | t [h] | Yield [%][c] |
---|---|---|---|---|
d.r.[d] | ||||
1 | ![]() |
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5 | 77 4:1 |
2 | ![]() |
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8 | 74 5:1 |
3 | ![]() |
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36 | 69 5:1 |
4 | ![]() |
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12 | 28 (64)[e] >25:1 |
5 | ![]() |
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6 | 72 3:1 |
6 | ![]() |
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12 | 58 4:1 |
Reaction conditions: 5a–f (0.2 mmol, 0.1m in degassed CH3NO2), 2a (1 mmol), 4a (2 mol%), irradiation with a 13 W fluorescent lightbulb at RT.
Only the major diastereoisomer shown.
Combined yields of the two isomers after chromatography.
Determined by 1H NMR analysis of the crude products (α/β).
Based on recovered 5d.