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10
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20644440282
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note
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[8a] Preparation of 15 by another route shown below was also studied with racemic compounds. This route is shorter than that of Scheme 2, and preparation of (S)-ii by hydrogenation (Equation Presented) of (R)-iii is reported by Vlad.
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11
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20644451912
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note
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[8b] However, it was later found that (R)-iii is not available even though both the enantiomers of iii are found in the Merck Index.
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12
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20644438108
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note
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[8c] Major companies including Merck now produce it as a racemic form.
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14
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0003601534
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Merck & Co., Inc., Whitehouse Station, NJ, Linalool
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[8e] The Merck Index, 12th ed. (Ed.: S. Budavari), Merck & Co., Inc., Whitehouse Station, NJ, 1996, 5520 Linalool.
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4444276636
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0141712450
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[11b] K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwona, K. Morikawa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768-2771.
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19
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21
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20644466930
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note
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3): δ= 175.0, 74.2, 72.9, 60.7, 33.3, 28.7, 20.0, 17.2, 14.1.
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22
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20644437407
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note
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1H NMR spectroscopy of the derived MTPA ester.
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24
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0001638723
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Iacono, S.1
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25
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20644434463
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note
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Alternatively, the following method afforded 15 in 17% yield from alcohol 13. (Equation Presented)
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27
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33845557915
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[17a] V. S. Martin, S. S. Woodard, T. Katsuki, Y. Yamada, M. Ikeda, K. B. Sharpless, J. Am. Chem. Soc. 1981, 103, 6237-6240.
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Sharpless, K.B.6
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28
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18844410382
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[17b] Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
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30
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20644459590
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note
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3) of 24: δ= 2.42 (dd, J = 13.5, 4 Hz, 1 H), 2.86 (dd, J = 13.5, 11 Hz, 1 H), 3.62-3.72 (m, 1 H), 4.07-4.24 (m, 1 H), 4.92-5.03 (m, 1 H), 6.25 (t, J = 8 Hz, 1 H), 6.35 (d, J = 8 Hz, 1 H).
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32
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0030661961
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[21a] T. Sunazuka, T. Hirose, Y. Harigaya, S. Takamatsu, M. Hayashi, K. Komiyama, S. Omura, P. A. Sprengeler, A. B. Smith, III, J. Am. Chem. Soc. 1997, 119, 10247-10248.
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0034603460
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0027421977
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