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disappearance of MOB (the time specified in Table 1). After the reaction was
complete, the reaction mixture was concentrated using rotary evaporator
under reduced pressure and the residue was purified by silica gel column
chromatography with 10% ethyl acetate in hexanes as eluent to furnish the
cycloadduct.
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17. NMR spectral data for the representative examples.
Compound 7a: 1H NMR (500 MHz, CDCl3): d 7.32–7.21 (m, 3H), 7.16–7.13 (m,
2H), 6.04 (dd, J = 2.5, 7.0 Hz, 1H), 3.43 (s, 3H), 3.41 (s, 3H), 3.41–3.37 (m, 1H),
3.33–3.31 (m, 1H), 3.27 (dd, J = 2.0, 7.0 Hz, 1H), 2.58 (ddd, J = 3.0, 9.5, 13.0 Hz,
1H), 1.85 (ddd, J = 3.0, 6.5, 13.5 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3): d
200.2, 143.2, 136.7, 128.7, 127.4, 127.0, 120.4, 93.5, 56.0, 50.7, 50.2, 48.2, 40.0,
30.1 ppm.
Compound 7c: 1H NMR (500 MHz, CDCl3): d 5.99 (dd, J = 1.5, 6.5 Hz, 1H), 3.98–
3.95 (m, 1H), 3.57 (dd, J = 2.5, 6.5 Hz, 1H), 3.53–3.47 (m, 1H), 3.44–3.39 (m, 1H)
3.37 (s, 3H), 3.31 (s, 3H), 3.16 (q, J = 3.0 Hz, 1H), 2.46 (ddd, J = 2.5, 8.0, 13.5 Hz,
1H), 1.56 (ddd, J = 3.0, 3.0, 13.5 Hz, 1H), 1.17 (t, J = 7.0 Hz, 3H) ppm; 13C NMR
(125 MHz, CDCl3): d 199.8, 136.0, 119.4, 93.4, 74.1, 64.4, 54.6, 50.8, 49.9, 46.9,
30.6, 15.3 ppm.
Compound 8e: 1H NMR (500 MHz, CDCl3): d 7.41–7.38 (m, 2H), 7.36–7.27 (m,
3H), 6.33 (dd, J = 2.0, 7.0 Hz, 1H), 3.64–3.59 (m, 1H), 3.38 (s, 3H), 3.33 (s, 3H),
3.32–3.29 (m, 1H), 3.26 (dd, J = 2.0, 6.5 Hz, 1H), 2.59 (ddd, J = 3.0, 9.5,14.0 Hz,
1H), 1.49 (ddd, J = 3.0, 5.5, 14.0 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3): d
199.1, 133.9, 132.1, 129.3, 127.8, 125.6, 124.4 93.8, 54.7, 50.9, 50.2, 49.3, 41.9,
28.9 ppm.
13. (a) Hypervalent Iodine Chemistry; Wirth, T., Ed.; Springer: Berlin, 2003; (b)
Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic: London, 1997.
14. General procedure: To a solution of a 2-methoxy-4-halophenol (0.5 mM) in
anhydrous MeOH (5 mL) was added DAIB (0.6 mM) at 0 °C under nitrogen
atmosphere. After 10 min stirring, a dienophile (10 mM) was added at the
same temperature and the stirring was continued. Then the temperature was
allowed to rise to RT, and the stirring was continued up to complete
Compound 9b: 1H NMR (500 MHz, CDCl3): d 6.61 (dd, J = 1.0, 6.5 Hz, 1H), 4.35
(dd, J = 3.0, 8.5 Hz, 1H), 3.95 (dt, J = 3.0, 8.0 Hz, 1H), 3.64–3.58 (m, 1H), 3.51 (dd,
J = 3.0, 6.5 Hz, 1H), 3.49–3.46 (m, 1H), 3.38 (s, 3H), 3.34 (s, 3H), 3.13–3.06 (m,
1H), 2.17–2.09 (m, 1H), 1.92 (m, 1H) ppm; 13C NMR (125 MHz, CDCl3): d 199.0,
134.5, 93.6, 93.1, 77.9, 69.3, 58.4, 54.7, 51.2, 50.0, 39.8, 29.4 ppm.
18. CCDC deposition No. 815225.