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33749017670
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In comparison with other methods for the synthesis of tetrahydropyrans it is noteworthy that 2,6-cis- and -trans-substituted tetrahydropyrans are formed with similar efficiency. The synthesis of trans-tetrahydropyrans in particular is often not trivial (for a recent successful example, refer to S. Roth, C. B. W. Stark, Angew. Chem. Int. Ed. 2006, 45, 6218-6221.)
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In comparison with other methods for the synthesis of tetrahydropyrans it is noteworthy that 2,6-cis- and -trans-substituted tetrahydropyrans are formed with similar efficiency. The synthesis of trans-tetrahydropyrans in particular is often not trivial (for a recent successful example, refer to S. Roth, C. B. W. Stark, Angew. Chem. Int. Ed. 2006, 45, 6218-6221.)
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23
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0041407526
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Frantz, D.E.1
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Carreira, E.M.3
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24
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34250845696
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Physical data for compound 7′. Colorless oil, a] D22, 19.9 (c, 1.00, CHCl3, Rf, 0.34 (hexane/Et2O, 75:25, 1H NMR (300 MHz, CDCl3, 25 °C, δ, 0.05 (s, 6 H, CH 3Si, 0.89 (s, 9 H, CH3CSi, 1.03-1.31 (m, 5H, 1.12 (d, J, 6.1 Hz, 3 H, CH3, 143-1.86 (m, 11 H, 2.19-2.24 (m, 2 H, 3.80 (m, 1 H, CHOH, 4.13 (m, 1H, CHOH) ppm. 13C NMR (75 MHz, CDCl3, 25 °C, δ, 4.8 (CH3, 4.4 (CH3, 18.1 (C, 18.8, 23.8, 25.0, 25.9, 25.9, 26.4, 28.1, 28.6, 38.8, 44.4, 67.4, 68.1, 80.3, 86.1 ppm. IR: ṽ, 3376, 2927, 2855, 1450, 1374, 1255, 1187, 1137, 1092, 1023, 893, 836, 774 cm -1. MS (CI, mlz, 339 (0.9, M, H, 321 (14.8, 281 (6.8, 189 (100, HRMS CI, C20H39O 2Si calcd. 339.2719
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2Si calcd. 339.2719; found 339.2712.
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25
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34250883120
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In compounds 7, 8, 9, 13, 14, and 4 there were no differences except for their degrees of optical rotation in the spectroscopic data for their (R) and (S) diastereoisomers.
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In compounds 7, 8, 9, 13, 14, and 4 there were no differences except for their degrees of optical rotation in the spectroscopic data for their (R) and (S) diastereoisomers.
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26
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34250843007
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Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany
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A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, Germany, 2004, volumes 1 and 2.
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de Meijere, A.1
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27
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0037039952
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D. Kim, J. Lee, P.J. Shim, J. I. Lim, T. Doi, S. Kim, J. Org. Chem. 2002, 67, 772-781.
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Kim, D.1
Lee, J.2
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Lim, J.I.4
Doi, T.5
Kim, S.6
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28
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24944529986
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Y. Kita, S. Matsuda, E. Fujii, M. Horai, K. Hata, H. Fujioka, Angew. Chem. Int. Ed. 2005, 44, 5857-5860.
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Kita, Y.1
Matsuda, S.2
Fujii, E.3
Horai, M.4
Hata, K.5
Fujioka, H.6
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29
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34250798906
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Their des were less than 50%.
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Their des were less than 50%.
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31
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34250831315
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-1, detection: 254 nm, retention time: 12.7 min [13 (R) isomer], 19.1 min [13′ (S) isomer].
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-1, detection: 254 nm, retention time: 12.7 min [13 (R) isomer], 19.1 min [13′ (S) isomer].
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