Temperature-controlled selectivity toward [1,3]- or [3,3]-sigmatropic rearrangement: Regioselective synthesis of substituted 3,4-dihydrocoumarins

Synlett

Volumn , Issue 18, 2009, Pages 2971-2976

  Liu, Yunkui ^a   Qian, Jianqiang ^a   Lou, Shaojie ^a   Xu, Zhenyuan ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

3,4 dihydrocoumarin; 1,3 sigmatropic rearrangement; 3,3 sigmatropic rearrangement; Gold catalyst; Tandem reaction

Indexed keywords

GOLD;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 72049127273     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218280     Document Type: Article

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73. Typical Experimental Procedure for the Synthesis of 2 under Condition A: AuCl3 (9.1 mg, 0.03 mmol), AgOTf (23.1 mg, 0.09 mmol), and DCE (2 mL) were added to a 10-mL flask. The mixture was stirred at r.t. for 5 min before a DCE solution of 1a (0.35 g, 1.0 mmol diluted in 1 mL of solvent) was added. Then the reaction mixture was stirred at 80 ?C for 4 h. Upon completion of the reaction, the resulting mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (200?300 mesh) using cyclohexane?EtOAc (12:1) as eluent to give pure 2a. Typical Experimental Procedure for the Synthesis of 3 under Condition B: AuCl3 (9.1 mg, 0.03 mmol), AgOTf (23.1 mg, 0.09 mmol), and DCE or DCB (2 mL) were added to a 10-mL sealed vessel. The mixture was stirred at r.t. for 5 min before a DCE or DCB solution of 1a (0.35 g, 1.0 mmol diluted in 1 mL of solvent) was added. Then the reaction mixture was stirred at 120 ?C for 2 h. Upon completion of the reaction, the resulting mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (200-300 mesh) using cyclohexane?EtOAc (12:1) as eluent to give pure 3a.
74. Representative Data for Compound 2 and 3: Compound 2b: white solid; Rf 0.46 (cyclohexane?EtOAc, 12:1); mp 198.3?201.0 ?C. 1H NMR (500 MHz, CDCl3): d = 4.32 (d, 2 H, J = 2.5 Hz, CH2), 7.25 (d, 1 H, J = 8.5 Hz, ArH), 7.43?7.85 (m, 9 H, ArH), 8.03 (t, 1 H, J = 2.5 Hz, ArCH=). 13C NMR (125 MHz, CDCl3): d = 26.12, 112.14, 117.50, 122.28, 122.91, 124.27, 125.25, 127.33, 128.87, 129.25, 130.76, 130.91, 131.74, 132.17, 133.55, 142.13, 147.77, 163.60. IR (KBr): 1711 (C=O), 1630 (C=C) cm?1. GC?MS: m/z = 364 [M+], 366 [M+ + 2]. HRMS (EI): m/z calcd for C20H13O2Br: 364.0099; found: 364.0113. Compound 3c: white solid; Rf 0.56 (cyclohexane?EtOAc, 12:1); mp 114.5?114.6 ?C. 1H NMR (500 MHz, CDCl3): d = 2.28 (s, 3 H, Me), 4.90 (s, 1 H), 5.72 (s, 1 H), 6.44 (s, 1 H), 6.89?7.33 (m, 8 H, ArH). 13C NMR (125 MHz, CDCl3): d = 20.80, 48.26, 117.04, 124.28, 127.52, 127.76, 128.96, 129.08, 129.26, 129.43, 134.53, 136.88, 140.77, 148.59, 163.26. IR (KBr): 1746 (C=O), 1627 (C=C) cm?1. GC?MS: m/z = 250 [M+]. HRMS (EI): m/z calcd for C17H14O2: 250.0994; found: 250.1001.
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