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. 2019 Mar 5;4(3):4856–4870. doi: 10.1021/acsomega.9b00333

Table 3. Lactonization Reaction Using cis- or trans-Stilbenea,b.

graphic file with name ao-2019-00333q_0003.jpg

        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
a

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.

b

Diasteromeric ratios (dr) were determined by 1H NMR analysis of the crude reaction mixture.