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Minolta Dynax 404SI

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Minolta Dynax 404si

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Supporting Information for Angew. Chem. Int. Ed. 200460822 Wiley-VCH 2004

69451 Weinheim, Germany

Direct Visual Detection of the Stereoselectivity of a Catalytic Reaction
Rienk Eelkema, Richard A. van Delden, and Ben L. Feringa*
[*] Prof. Dr. B. L. Feringa, R. Eelkema, Dr. R. A. van Delden Department of Organic and Molecular Inorganic Chemistry Stratingh Institute, University of Groningen Nijenborgh 4, 9747 AG Groningen (The Netherlands)
Fax: (+31)503634296 E-mail: Feringa@chem.rug.nl
General experimental remarks: Reagents were purchased from Aldrich, Acros Chimica, Strem, Merck or Fluka and were used as provided unless otherwise stated. All solvents were reagent grade and were dried and distilled before use according to standard procedures. Chromatography: silica gel, Merck type 9385 230-400 mesh, TLC: silica gel 60, Merck, 0.25 mm. Optical rotations were measured on a Perkin Elmer 241 MC at ambient temperature. Mass spectra (HRMS) were recorded on an AEI MS-902 by Mr. A. Kiewiet. HPLC analyses were performed on a Shimadzu 10AD-VP using the chiral columns as mentioned. Preparative HPLC was performed by Mr. M. B. van Gelder or Ms. T. D. Tiemersma-Wegman on a preparative Gilson HPLC system consisting of a 231XL sampling injector, a 306 (10SC) pump, an 811C dynamic mixer, a 805 manometric module, with a 119 UV-VIS detector and a 202 fraction collector, using the chiral columns as mentioned. Melting points were recorded on a Bchi B-545 melting point apparatus.
C NMR spectra were recorded on a Varian Gemini-200 (50.32 MHz) or a Varian 300 (75.48
MHz) spectrometer in CDCl3. Chemical shift values are denoted in values (ppm) relative to residual solvent peaks (CHCl3, 1H =7.26, 13C =77). The liquid crystalline material E7 was received as a gift from Merck, Darmstadt. The pitch of the liquid crystalline (LC) phases and thus indirectly the helical twisting
power (HTP) of the chiral dopants was determined by Grandjean-Cano technique, using plane-convex lenses of known radii (R = 25.119, 30.287, 40.388 or 50.481 mm, Linos Components; Radiometer), and an Olympus BX 60 microscope. LC phases were aligned on a glass surface (typically 6.25 cm2) that was spincoated with commercially available polyimide AL1051 (purchased from JSR, Belgium) and linearly rubbed with a velvet cloth. Reflection measurements were performed on a JASCO J715 Spectrophotometer equipped with a fluorescence extension (a photomultiplier perpendicular to the direction of the light). This spectrophotometer was adapted to hold LC covered glass plates in such a way that both the incident light beam and the photomultiplier tube were at an angle of 45 to the surface. Actual photographs of the coloured LC phases were taken at an angle of 90 using a Minolta Dynax 404si Single Lens Reflex camera equipped with a Minolta AF 100mm MACRO 1:2.8(32) lens and Kodak Gold iso 100/21 film.
1-Bromo-4-heptyloxy-benzene, S1
A mixture of n-heptylbromide (20 g, 111.7 mmol), 4-bromophenol (30 g, 173.4 mmol), potassiumcarbonate (30 g, 217.4 mmol) and acetone (400 ml) was refluxed for two days. After the reaction mixture was allowed to cool down to room temperature, it was filtered and the solvent was removed by evaporation. The remaining oil was solved in dichloromethane and washed with 2 x 20 ml 2 M NaOH (aq). The organic layer was dried over Na2SO4 and the solvent was evaporated. The oil again was solved in chloroform, washed with 2 x 20 ml 2 M NaOH (aq), dried with Na2SO4 and the solvent was again evaporated, yielding S1 as a colourless oil (29.4 g, 97%). 1H NMR (300 MHz, CDCl3) 7.36 (d, J = 9.15 Hz, 2H), 6.77 (d, J = 8.79 Hz, 2H), 3.91 (t, J = 6.59 Hz, 2H), 1.77 (dt, J1 = 7.69 Hz, J2 = 6.59 Hz, 2H), 1.44-1.31 (m, 8H), 0.90 (t, J = 6.96 Hz, 3H); 13C NMR (50.32 MHz, CDCl3) 158.2, 132.1, 116.2, 112.5, 68.2, 31.7, 29.1, 29.0, 25.9, 22.6, 14.1; MS (EI): m/z 272 (M+, 30%), 270 (M+, 30%), 174 (MC7H14, 98%), 172 (MC7H14, 100%), 157 (MOC7H15, 4%), 155 (MOC7H15, 4%); HRMS calcd for C13H19OBr: 270.062; Found 270.061.

1-(4'-Heptyloxy-biphenyl-4-yl)-ethanone, S2
To a solution of bromide S1 (2.2 g, 8.1 mmol) in 15 ml of dry DME Pd(PPh3)4 (192 mg, 0.17 mmol, 2 mol%) and 10.2 ml Na2CO3 (aq) (2
20.3 mmol) were added. This mixture was stirred for 15 min, after
which 4-acetylphenylboronic acid (12.2 mmol, 2.0 g) was added. After the mixture had refluxed overnight, the solution was allowed to cool to room temperature and was transferred to a separatory funnel. The water layer was extracted with 3 x 15 ml CHCl3, the combined organics were washed with brine, dried over Na2SO4 and the solvent was evaporated. The remaining brown crystals were recrystallised from ethanol, yielding S2 as grey crystals (1.8 g, 71%). m.p. 136.8 - 138.0 C; 1H NMR (300 MHz, CDCl3) 8.00 (d, J = 8.06 Hz, 2H), 7.64 (d, J = 8.42 Hz, 2H), 7.56 (d, J = 8.43 Hz, 2H), 6.99 (d, J = 8.79 Hz, 2H), 4.00 (t, J = 6.59 Hz, 2H), 2.63 (s, 3H), 1.82 (dt, J1 = 6.59 Hz, J2 = 7.32 Hz, 2H), 1.41 (m, 8H), 0.90 (t, J = 6.59 Hz, 3H); 13C NMR (50.32 MHz, CDCl3) 197.7, 159.5, 145.4, 135.2, 131.9, 128.9, 128.3, 126.5, 114.9, 68.1, 31.8, 29.2, 29.0, 26.6, 26.0, 22.6, 14.1; MS (EI): m/z 310 (M+, 85%), 295 (MCH3, 3%), 238 (MCOCH3C2H5, 4%), 152 (C6H4C6H4, 13%), and 115 (C7H15O, 3%); HRMS calcd for C21H26O2: 310.193; Found 310.193.
1-(4'-Heptyloxy-biphenyl-4-yl)-3-phenyl-propenone, 3
NaOH (208 mg, 5.2 mmol) was dissolved in 5 ml 30% EtOH (aq). S2 (800 mg, 2.6 mmol) and benzaldehyde (547 mg, 5.2 mmol) were added while stirring at room temperature. The mixture was heated to 30 C and stirred for two days, after which water (10 ml) and CH2Cl2 (15 ml) were added to the grey suspension. The water layer was extracted with 3 x 15 ml CH2Cl2, the combined organics were washed with brine, dried over Na2SO4 and the solvent was evaporated. The remaining green crystals were
recrystallised from toluene and subsequently filtered with CH2Cl2 over a 4 cm plug of silica, yielding 3 as yellow crystals (735 mg, 71%). m.p. 142.6 143.0 C; 1H NMR (300 MHz, CDCl3) 8.09 (d, J = 8.06 Hz, 2H), 7.85 (d, J = 15.87 Hz, 1H), 7.64 (m, 7H), 7.43 (m, 3H), 7.00 (d, J = 8.55 Hz, 2H), 4.01 (t, J = 6.60 Hz, 2H), 1.82 (dt, J1 = 6.59 Hz, J2 = 7.57 Hz, 2H), 1.39 (m, 8H), 0.90 (t, J = 7.08 Hz, 3H); 13C NMR (50.32 MHz, CDCl3) 189.8, 159.5, 145.2, 144.5, 136.2, 135.0, 132.0, 129.1, 128.9, 128.4, 128.3, 126.6, 122.0, 114.9, 68.1, 31.8, 29.2, 29.0, 26.0, 22.6, 14.1; MS (EI): m/z 398 (M+, 100%), 299 (MC7H15, 58%); HRMS calcd for C28H30O2: 398.225; Found 398.223. Anal. calcd. for C28H30O2: C, 84.38; H, 7.59%. Found: C, 84.4, H, 7.7%.
1-(4'-Heptyloxy-biphenyl-4-yl)-3-phenyl-pentan-1-one, 4
Prepared according to the general procedure using Cu(OTf)2 (2.7 mg, 7.46 mol, 5.0 mol%), Ligand racL1 (6.30 mg, 15.2 mol, 10.0 mol%), dichloromethane (5 ml), 3 (70 mg, 0.18 mmol) and Et2Zn (0.3 ml). The crude product was purified by column chromatography (SiO2, pentane : CH2Cl2 = 1:1), yielding 4 as a white solid (60 mg, 80%). m.p. 98.8 - 99.4 C (Racemate); 1H NMR (300 MHz, CDCl3) 7.95 (d, J = 8.79 Hz, 2H), 7.60 (d, J = 8.55 Hz, 2H), 7.55 (d, J = 9.03 Hz, 2H), 7.25 (m, 5H), 6.97 (d, J = 8.79 Hz, 2H), 4.00 (t, J = 6.59 Hz, 2H), 3.27 (m, 3H), 1.74 (m, 4H), 1.41 (m, 8H), 0.90 (t, J = 6.60 Hz, 3H), 0.81 (t, J = 7.56 Hz, 3H); 13C NMR (50.32 MHz, CDCl3) 198.7, 159.4, 145.2, 144.7, 135.2, 131.9, 128.6, 128.4, 128.2, 127.6, 126.5, 126.2, 114.9, 68.1, 45.5, 43.0, 31.8, 29.2, 29.2, 29.0, 26.0, 22.6, 14.1, 12.1; MS (EI): m/z 428 (M+, 66%), 399 (MC2H5, 27%), 310 (MCH3C2H2C6H5, McLafferty, 100%), 295 (MCH2C3H6C6H5, 47%); HRMS calcd for C30H36O2: 428.272; Found 428.272; Anal. calcd. for C30H36O2: C, 84.07; H, 8.47%. Found: C, 83.8; H, 8.7%; HTPE7 = 18.5 m1; []D (84% ee) = +14.9 (c = 0.40, CHCl3); Enantioresolution of 4 was accomplished by preparative chiral HPLC (Chiralcel OD, n-heptane:IPA = 90:10, 1 ml/min.). retention times: 6.7 (minor) and 13.8 min (major).

 

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