, 5 Hz), 132.1 (d, J = 2.0 Hz), 130.8 (d, J = 2.0Hz), 128.6 (d, J = 12.2 Hz), MHz, CDCl3) ? (ppm): 135.5 (d, J = 11.7 Hz), vol.132
Data were collected, using a microfocus sealed tube of Mo K? radiation ,
, 34A (Bruker AXS Inc.). Data reduction was performed using SAINT v8.34A (Bruker AXS Inc.). Correction for absorption was performed using multi-scan integration as, and SAINT v8, pp.10-10, 2013.
, Structure solutions were found by charge flipping methods (SUPERFLIP
2012)) and refined with (SHELXL) ,
, Mercury drawing of the crystalline structure of 168 obtained by X-Ray diffraction analysis
, , vol.892, p.98
, Pd(OAc)2 (11.2 mg, 0.05 mmol, 0.1 eq.), Bu4NCl (152 mg, 0.55 mmol, 1.1 eq.), NaHCO3 (113 mg, 1.35 mmol, 2.7 eq.concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (50/50: cyclohexane/ethyl acetate, Acrylate 197 (107 mg, 0.75 mmol, 1.5 eq.)
, m, 4H), 7.38-7.35 (m, 1H, vol.7
, C NMR (75.3 MHz, CDCl3) ? (ppm): 168.9, 165.9, 1016.
, , vol.278, p.16
, ) was dissolved in 9 mL of MeOH and Pd/C (137 mg, 0.13 mmol, 0.3 eq.) was added to the mixture. The reaction was stirred 4 days under a hydrogen atmosphere (1 atm), filtered over Celite before removing the solvent in vacuo. The residue was purified by silica gel flash chromatography (90/10: dichloromethane/methanol and 1% of triethylamine
, 300 MHz, MeOD) ? (ppm): 7.47-7.42 (m, 2H), 7.28-7
2.94 (dd, J = 13.9 Hz, J = 9.0 Hz, 1H), 1.90 (s, 3H), 1.62 (s, 6H), Hz, 1H), 3.69 (s, 3H), 3.16 (dd, J = 13.9 Hz, J = 5.6 Hz, 1H), vol.202 ,
, was collected and the solvent was removed under reduced pressure, affording the 5-bromo-2-(pyridin-2-yl)quinolone (131 mg, 0.28 mmol, 93%) as an off-white solid
, Hz, 1H), 7.85 (dd, J = 7.5 Hz, J = 1.0 Hz, 1H), 7.61 (dd, J = 8.5 Hz, J = 7.6 Hz, 1H), vol.7
, eq.) were added to a vial armed with a magnetic stir bar. The vial was purged with nitrogen three times before adding 2 mL of dry dioxane. The reaction was stirred 18h at 110°C. The vial was then cooled to room temperature, diluted by CH2Cl2, washed with brine, dried with MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (cyclohexane/dichloromethane, vol.60, p.40
, 56 %) as a yellow solid. 1 H NMR (300 MHz, CDCl3) ? (ppm): 8.74 (ddd, J =, vol.4
, Hz, 1H), vol.7
, Hz, 2H), 6.07 (dd, J = 8.0 Hz, J = 1.5 Hz, 2H). 13 C NMR (75.3 MHz, CDCl3) ? (ppm): 149.9, pp.238-239
, , vol.236
, , vol.380, p.0
, H NMR spectra was consecutively recorded. 1 H NMR, vol.300
, CDCl3) ? (ppm): 8.46 (dt, J = 7.7 Hz, J = 1.1 Hz, 2H), 8.15-8.07 (m, 4H), 7.35 (ddd, J = 7
, , vol.5
, Exp 1, step 1 376 (16.8 mg, 25 µmol), vol.373
, Exp 2, step 1 376 (16.8 mg, 25 µmol), 373 (6.1 mg, 25 µmol)
, Exp 3
8 mg, 25 µmol), 373 (6.1 mg, 25 µmol) ,
, Exp 4, step 1 376 (16.8 mg, 25 µmol), vol.373
, Exp 5, step 1 376 (16.8 mg, 25 µmol), vol.373
, Exp 6, step 1 376 (15.0 mg, 22 µmol), vol.373
, Methoxy-1,1'-binaphthalene, vol.378
, The reaction was stirred at 50°C for 16h. The solvent was evaporated under reduced pressure, and the residue was purified by preparative TLC (90/10 : cyclohexane/ethyl acetate, Rf : 0.7) to give the product 378 as a colorless oil. The yield was calculated over the two steps of Pathway II. Enantiomeric excess was determined by Chiral HPLC analysis, The vial was purged three times with nitrogen and CH3CN (1 mL) was added
, 374 (5.1 mg, 25 µmol), CsF (7.6 mg, vol.50
, mg (27%) (AT676) -8%
, .1 mg, 25 µmol), CsF (7.6 mg, 50 µmol) 0 mg (0%) (AT708), vol.2, p.379
, .1 mg, 25 µmol), CsF (7.6 mg, 50 µmol) 2.0 mg (28%) (AT727) -8%, vol.3, p.379
, CsF (7.3 mg, 48 µmol) 0 mg (0%) (AT748), vol.374
, CsF (7.3 mg, 48 µmol) 0 mg (0%) (AT808), vol.374
, CsF (6.8 mg, 48 µmol) 0 mg (0%) (AT810), vol.374
, Experiments with the chiral complex Au(I), vol.379
4S)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-5,5-dimethyl-4-(1-methylethyl)-oxazole]gold(I), vol.379 ,
, , vol.633
, Under inert atmosphere, (4S)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-5,5-dimethyl-4-(1-methylethyl)-oxazole (80.2 mg, 0.2 mmol, 1.0 eq.) and chloro(dimethylsulfide)gold(I)
, The reaction mixture was stirred in the dark for 2 hours. Then, the solvent was removed under reduced pressure and the residue was triturated in pentane to give product 379 (118.6 mg, 0.19 mmol, 95%) as a white solid. 1 H NMR (300 MHz, CDCl3) ? (ppm
HRMS (ESI/TOF + ) C26H28AuClNOP [M+Na] + calculated 656.1154 found 656.1158. Slow vapor diffusion of Et2O in a solution of 379 in CH2Cl2 allowed to produce suitable monocrystals for X-ray diffraction analysis, Hz, 6H). 31 P NMR (121.5 MHz, CDCl3) ? (ppm): 33.5. 13 C NMR (75 MHz, CDCl3) ? (ppm): 134.8 (d, J = 7.2 Hz), 134.4 (d, J = 6.9 Hz), 134.2 (d, J = 6.9 Hz), 131.3 (m), 130.8 (m), 130.6 (m) ,
, Data were collected, using a microfocus sealed tube of Mo K? radiation (k = 0.71073 Å) on a KappaCCD diffractometer. Data collection and cell refinement were performed using, Bruker APEX 2 DUO. A single crystal was mounted and immersed in a stream of nitrogen gas, vol.150
, Structure solutions were found by charge flipping methods (SUPERFLIP
2012)) and refined with (SHELXL) ,
, this structure has been deposited with the Cambridge Crystallographic Data
, Mercury drawing of the crystalline structure of 379 obtained by X-Ray diffraction analysis 2-Methoxy-1,1'-binaphthalene 378, vol.379
, , vol.284, p.12
, Pathway, vol.1, pp.655-657
, mL) was added. The reaction was stirred at 50°C for 16h. The mixture was filtered throught a celite pad and the filtrate was evaporated under reduced pressure. Then, the residue was triturated with pentane to give the intermediate crude product 2-methoxynaphtyl, The vial was purged three times with nitrogen and CH3CN
, MHz, CD3CN) ? (ppm): 21.7, 20.0. Then
, The vial was purged three times with nitrogen and CH3CN (1 mL) was added. The reaction was stirred at 50°C for 16h. The solvent was evaporated under reduced pressure and the residue was purified by preparative TLC (90/10 : cyclohexane/ethyl acetate, eq.) and CsF (7.6 mg, 0.05 mmol
, min, plus sign was arbitrary attributed if the major enantiomer of 378 corresponded to the HLPC pic with the lower retention time, and minus sign in the opposite case, 0mL/min): +1% ee (retention times: 4.4 min and 4, vol.7
, , vol.264, p.12
, Pathway, vol.1, pp.655-658
, The reaction was stirred at 50°C for 16h. The mixture was filtered throught a celite pad and the filtrate was evaporated under reduced pressure. Then, the residue was triturated with pentane to give the intermediate crude product 2-methoxynaphtyl-[(4S)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-5,5-dimethyl-4-(1-methylethyl)-oxazole]gold(I) (30.0 mg, 0.039 mmol, 78%) as a white solid, which was engaged in the following step without further purification. 1 H NMR (300 MHz, CDCl3) ? (ppm): 8.47 (d, J = 8.1 Hz, 1H), The vial was purged three times with nitrogen and CH3CN (1 mL) was added
, 24 (s, 3H), 1.16 (s, 3H), 0.74 (d, J = 6.5 Hz, 3H), 0.68 (d, J = 6.5 Hz, 3H), Hz, 1H), 1.33-1.30 (m, 1H), vol.1, p.2
, The vial was purged three times with nitrogen and CH3CN (1 mL) was added. The reaction was stirred at 50°C for 16h. The solvent was evaporated under reduced pressure and the residue was purified by preparative TLC (cyclohexane, Rf : 0.5) to give product 386 in mixture with multiple side-products
, A second purification by preparative TLC did not improved the purity of the sample, vol.387
, , vol.713, p.6
, mg, 0.1 mmol, 1.0 eq.) and chloro(dimethylsulfide)gold(I) (29.5 mg, 0.1 mmol, 1.0 eq.) were dissolved in dichloromethane (1 mL). The reaction mixture was stirred in the dark for 2 hours. Then, the solvent was removed under reduced pressure and the residue was, p.300
, CDCl3) ? (ppm): 7.77-7.70 (m, 2H), 7.53-7.36 (m, 8H), vol.5, p.7
, = 6.5 Hz, 1H), 0.91 (d, J = 6.7 Hz, 3H), 0.81 (d, J = 6.7 Hz, 3H). 31 P NMR (121.5 MHz, CDCl3) ? (ppm): 30.5. 13 C NMR (75 MHz, CDCl3) ? (ppm): 163.0, vol.134
,
, Methoxy-1,1'-binaphthalene 378 (from 387): C21H16O, M =, vol.284, p.12
, Rf : 0.5) to give product 389 (2.0 mg, 0.010 mmol, 21%) as a white solid. 1 H NMR (300 MHz, CDCl3) ? (ppm
Hz, 1H), 2.69 (dd, J = 13.7 Hz, J = 6.3 Hz, 1H), 1.92-1.79 (m, 3H), 1.49-1.52 (m, 1H). The spectral data was, vol.6 ,
, isopropanol/hexane 1/99, flow rate 1.0mL /min): <1% e.e. (retention times: 7.2 min and 7.5 min)
, Experiment with 390 as catalyst: 2-(4-Methoxybenzyl)tetrahydrofuran, vol.389, pp.1010-1011
, , p.12
, The reaction was placed inside the turned-off photochemical reactor and stirred under blue light irradiation for 2h. The mixture was filtered and the filtrate was evaporated under reduced pressure. Then, the residue was triturated with diethyl ether to give the intermediate crude product [(4-methoxyphenyl)-((4S)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-5,5-dimethyl-4-(1-methylethyl)-oxazole)]chloro gold(III) tetrafluoroborate (40 mg) as an orange solid, which was engaged in the following step without further purification. 1 H NMR (300 MHz, The vial was purged three times with nitrogen and CH3CN (1 mL) was added
, 67 (s, 3H), 1.61 (s, 3H), 0.95 (d, J = 7.1 Hz, 3H), 0.21 (d, J = 6.8 Hz, 3H). 31 P NMR (121.5 MHz, CD2Cl2) ? (ppm): 21.0. A NMR tube was charged with 4-penten-1-ol, Hz, 1H), 3.64 (s, 3H), 1.99-1.88 (m, 1H), vol.1
, NaHCO3 (8.4 mg, 0.1 mmol, 2 eq
, The tube was shaken for 16h at room temperature. The solvent was evaporated under reduced pressure and the residue was purified by preparative TLC (80/20 : cyclohexane/ethyl acetate, Rf : 0.6) to give product 389 (1.0 mg, 0.005 mmol, 10%) as a white solid, The NMR tube was purged three times under nitrogen
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