Table 3. Lactonization Reaction Using cis- or trans-Stilbenea,b.
diastereomer |
|||||||
---|---|---|---|---|---|---|---|
entry | conditions | 1s | 3 (%) | A | B | C | D |
1 | cis-selective conditions | Z | 49 | 52 | 9 | 22 | 17 |
2 | E | 70 | 43 | 24 | 21 | 12 | |
3 | trans-selective conditions | Z | 41 | 52 | 31 | 0 | 17 |
4 | E | 73 | 53 | 35 | 0 | 18 |
Reaction conditions: cis-selective conditions: 1 (2 equiv), 2a (0.3 mmol), I2 (0.3 mmol), and Ca(OH)2 (0.3 mmol) in tBuOH (3 mL) were stirred at ambient temperature and irradiated with a compact fluorescent lamp (CFL) for 20 h. trans-Selective conditions: 1 (2 equiv), 2a (0.3 mmol), I2 (0.3 mmol), and Na2CO3 (0.3 mmol) in tBuOH (2 mL) and H2O (1 mL) were stirred at ambient temperature and irradiated with compact fluorescent lamps (CFLs) for 20 h.
Diasteromeric ratios (dr) were determined by 1H NMR analysis of the crude reaction mixture.