Scope of DDQ/TBN-catalyzed aerobic allylation of isochromans 6a.
Entry | Product | Yield (%) | ||
---|---|---|---|---|
8b | 8′ | |||
1 | 8b | 76 | 8 | |
2 | 8c | 80 (2.2 : 1)c | 7 | |
3 | 8d | 72 (2.9 : 1)c | 10 | |
4 | 8e | 50 (75) | 14 | |
5 | 8f | 66 (90) | — | |
6 | 8g | 48 | 42 | |
7 | 8h | 18 (30) | — | |
8 | 8i | 33 (54) | — | |
9 | 8j | 34 (49) | — | |
10 | 8k | 41 (59) | — | |
11 | 8l | 37 (52) | — | |
12 | 8m | 12 (22) | — | |
13 | 8n | NRd | — | |
14 | 8o | NRd | — |
Reaction conditions: (i) 6 (0.37 mmol), DDQ (0.074 mmol), TBN (0.074 mmol), O2, DCE (3.7 mL), 0 °C or rt, 36 h; (ii) allyltributyl stannane (0.75 mmol), LiPF6 (0.19 mmol), MSA (0.075 mmol), 80 °C, 24 h.
Isolated yield. Yields in the parentheses are based upon recovered starting material.
Only the diastereomeric ratio was obtained by the analysis of 1H NMR spectrum.
No reaction.