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| General Procedure for Diels¨CAlder Reactions (9, 10). Vacuum-dried resin 3 (800 mg, 0.86 meq, 1.0 eq) was swollen with CH2Cl2 (20 mL) for 10 min, then cooled to 0 ¡ãC. Solid m-CPBA (580 mg, 2.58 mmol, 3.0 eq) was added and the reaction was stirred at 0 ¡ãC for 1 h, then allowed to warm to RTand stirred for 6 h. The resin was washed and dried, then swollen with CH2Cl2 (200 mL) for 10 min. A stock solution of Grubbs¡¯ second-generation catalyst (0.1 M in degassed toluene, 5.1 mL, 0.51 mmol, 0.6 eq) was added and the mixture stirred at 80 ¡ãC overnight. The resin was cooled, washed, and dried, then swollen in toluene (20 mL). For 9, N-phenylmaleimide (1.14 g, 6.6 mmol, 7.7 eq) was added and the mixture was stirred at 80 ¡ãC for 36 h. The resin was cooled, washed, and dried to afford benzodipyrrolidines 9. |
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