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41349088124
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This ratio was determined from the 1H NMR spectra of the crude mixture at the end of reaction time, by integration of the signals corresponding to H-5 and H-6 of each stereoisomer
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1H NMR spectra of the crude mixture at the end of reaction time, by integration of the signals corresponding to H-5 and H-6 of each stereoisomer.
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17
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0010609011
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41349093318
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The adduct 3 did not afford suitable crystals for their study by single-crystal X-ray analysis. Hence, this compound was analyzed using X-ray powder diffractometry to determine its crystalline structure. The powder was loaded into the holder (3 mm thick) and pressed slightly with a glass slide to ensure a flat surface and thus the absence of instrumental shift in the position of peaks in the diffractogram. The operating conditions for the data collection were: Cu Kα incident radiation (λ, 1.54183 Å, 5-70° scanning interval, 0.02° step size, and 40 s count time per step, using a Philips PW-1800 diffractometer equipped with a graphite secondary monochromator. The compound crystallized in the monoclinic system, with the space group C2, one molecule in the asymmetric unit giving four molecules in the unit cell (Z, 4, and the following unit cell dimensions: a, 23.8333 (10) Å, b, 10.0745 (4) Å, c, 14.3027 (6) A
-
The adduct 3 did not afford suitable crystals for their study by single-crystal X-ray analysis. Hence, this compound was analyzed using X-ray powder diffractometry to determine its crystalline structure. The powder was loaded into the holder (3 mm thick) and pressed slightly with a glass slide to ensure a flat surface and thus the absence of instrumental shift in the position of peaks in the diffractogram. The operating conditions for the data collection were: Cu Kα incident radiation (λ = 1.54183 Å), 5-70° scanning interval, 0.02° step size, and 40 s count time per step, using a Philips PW-1800 diffractometer equipped with a graphite secondary monochromator. The compound crystallized in the monoclinic system, with the space group C2, one molecule in the asymmetric unit giving four molecules in the unit cell (Z = 4), and the following unit cell dimensions: a = 23.8333 (10) Å, b = 10.0745 (4) Å, c = 14.3027 (6) Å, and β = 113.28 (1)°. As starting configuration was used the molecule optimized by molecular modelling with a semiempirical quantum chemistry model [code HyperChem: HYPERCHEM. Release 5. Standalone Version. Computational Chemistry, Hypercube Inc., Publication HC50-00-03-00, October 1996, ISBN 1-896164-17-X]. The structure was solved by direct-space methods with a 'Monte-Carlo/parallel tempering' search algorithm [code FOX: Favre-Nicolin, V.; Cern, R. FOX: a program for ab initio structure solution from powder diffraction data. Laboratory of Crystallography, University of Geneva, Switzerland, 2000], followed by a final refinement using the Rieltved method [code FullProf: Rodríguez-Carvajal, J. FULLPROF: a program for Rietveld refinement and pattern matching analysis. Abstracts of the Satellite Meeting on powder diffraction of the XV Congress of the International Union of Crystallography, Toulouse, France, 1990].
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23
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41349103835
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+) resin.
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+) resin.
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24
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0042738074
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25
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33746660241
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Lautens, M.1
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Colucci, T.J.3
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28
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41349108197
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Selected Data for Compound 3 White solid; 43% yield; [α]D20 -27.2 (c 0.51, CHCl3, mp 189-190°C. 1H NMR (400 MHz, CDCl3, δ, 6.40 (d, 1 H, J5,6, 5.6 Hz, H-6, 6.24 (d, 1 H, H-5, 4.77 (dd, 1 H, J1′,2, 11.3 Hz, H-1′, 4.35 (d, 1 H, J2,3, 3.4 Hz, H-3, 2.97 (dd, 1 H, H-2, 13C NMR (100 MHz, CDCl3, δ, 143.1 (C-6, 136.6 (C-5, 92.8 (C-3, 88.5, 87.9 (C-1, C-4, 51.3 (C-2, HRMS (CI, m/z calcd for C 23H31NO13Na [M, Na, 552.1693; found: 552.1689. Selected Data for Compound 7d Pale yellow oil; 60% yield; [α]D20 +29.4 (c 0.54, CHCl 3, 1H NMR (400 MHz, CDCl3, δ, 5.57 (dd, 1 H, J1′,2′, 2.4 Hz, H-1′, 5.37 (ddd, 1 H, H-2′, 5.11 dd, 1
-
+: 488.1768; found: 488.1754.
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