Table 3.
Synthesis of chromenes by the 1,4-addition of boronic acids to β-(2-hydroxyaryl)enones [34].
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| entry | R1 | R2 | R3 | Ar | additive (equiv) | yield A + B (%) ratio A/B |
yield C (%) | ee C (%) |
| 1 | H | Me | Me | Ph | – | 99 (1:13) | 90 | 96 |
| 2 | H | Me | Me | 4-MeO-C6H4 | AgBF4 (0.1) | 96 (1:13) | 90 | 97 |
| 3 | H | Me | Me | 3-MeO-C6H4 | AgBF4 (0.1) | 96 (1:13) | 94 | 97 |
| 4 | H | Me | Me | 3,4-(CH2O2)-C6H3 | AgBF4 (0.1) | 99 (1:16) | 89 | 98 |
| 5 | H | Me | Me | 4-Me-C6H4 | – | 99 (1:13) | 94 | 97 |
| 6 | H | Me | Me | 4-Ac-C6H4 | AgBF4 (0.1) | 99 (1:16) | 90 | 96 |
| 7 | H | H | Ph | Ph | – | 99 (2:1) | 92 | 99 |
| 8 | H | OMe | Me | Ph | – | 99 (1:16) | 94 | 95 |
| 9 | t-Bu | t-Bu | Me | Ph | – | 94 (1:99) | 90 | – |
